FR2818646A1 - NOVEL C-GLYCOSIDE DERIVATIVES AND USE - Google Patents

Abstract

The invention concerns novel C-glycoside derivatives, cosmetic, hygienic or pharmaceutical compositions containing them and their use as amphiphilic agents and in particular as emulsifiers and/or surfactants. The invention also concerns the use of C-glycoside derivatives as agents capable of forming lamellar phases resulting in lipid vesicles and compositions containing them.

Description

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The present invention relates to novel C-glycoside derivatives, to cosmetic, hygienic or pharmaceutical compositions comprising them and to their use as amphiphilic agents and in particular as emulsifiers and / or surfactants.

Another subject of the invention relates to the use of C-glycoside derivatives as agents capable of forming lamellar phases leading to lipid vesicles as well as to the compositions comprising them.

For various reasons related in particular to a better comfort of use (softness, emollience and others), the current cosmetic and dermatological compositions are most often in the form of an oil-in-water type emulsion (O / W). ) consisting of an aqueous dispersant continuous phase and an oily dispersed discontinuous phase or a water-in-oil (W / O) type emulsion consisting of an oily dispersant continuous phase and an aqueous dispersed discontinuous phase. O / W emulsions are the most in demand in the cosmetic and / or dermatological field because they comprise, as an external phase, an aqueous phase, which gives them, when applied to the skin, a cooler feel. less fat and lighter than W / O emulsions.

The emulsions are generally stabilized by suitable emulsifying surfactants which, thanks to their amphiphilic structure, are placed at the oil / water interface and thus stabilize the dispersed droplets. These emulsifiers, however, have the disadvantage of being potentially irritating to the skin, the eyes and the scalp, including for sensitive skin subjects.

Thus, for many years, in the cosmetic and / or dermatological industry, new amphiphilic derivatives having a good cutaneous tolerance have been sought. In this respect, many families of surfactants have already been described; a description thereof can be found, for example, in "Surfactants in cosmetics", 1985, Surfactant science series, Volume 16, Martin M.

Rieger Ed., And particularly the part treated by Bernard Idson pages 1-28.

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Les propriétés des tensioactifs varient en fonction de la prédominance du groupe lipophile ou du groupe hydrophile. Les tensioactifs possèdent différents pouvoirs bien connus de l'homme du métier parmi lesquels on peut citer le pouvoir mouillant, le pouvoir émulsionnant, le pouvoir solubilisant, le pouvoir détergent et le pouvoir moussant.

The properties of the surfactants vary depending on the predominance of the lipophilic group or the hydrophilic group. The surfactants have various powers well known to those skilled in the art, among which mention may be made of the wetting power, the emulsifying power, the solubilizing power, the detergency and the foaming power.

In addition to the fact that known surfactants often have significant side effects, it remains interesting to have new amphiphilic derivatives that are not very aggressive for the skin and that make it possible to make cosmetic and / or dermatological compositions that are softer for the skin and / or have a good tolerance. cutaneous Among the anionic surfactants, the anionic derivatives of alkylpolyglucosides (APG) are known to provide interesting properties such as a very good skin tolerance and a good foaming and detergent power.

The objective of the invention is to have new amphiphilic derivatives allowing in particular to achieve O / W and W / O emulsions and having good cosmetic properties and good skin tolerance.

Over the last twenty years, the chemistry of C-glycoside derivatives has grown considerably.

There are two main reasons for this interest; unlike the O-glycoside derivatives, the C-glycoside derivatives are perfectly stable in biological media because they are not metabolizable; It has also been shown that the C-glycosidic structures have conformational properties very close to their O-glycoside analogues (see in particular the "C-glycoside synthesis", Postema M.H.D., CRC Press, 1995).

C-glycoside derivatives are well known in the scientific literature; the following publications may notably be cited:

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Allevi et ai. (J. Chem. Soc., Chem. Commun., 1987, pp. 101-102) qui décrit des dérivés de C-glucopyranosyles ; - Nakamura et al. (Tetrahedron Letters, 1996, 37, pp. 3153-3156) ; Tsang et ai. (J. Org. Chem. 1985, 50, pp. 4659-4661) décrit des dérivés pyranose bicycliques ; - Lay et al. (J. Chem. Soc., Perkin Trans. 1., 1994, pp. 333-338) qui décrit des dérivés de disaccharides ;

- Karagiri et al. (J. Chem. Soc., Perkin Trans. 1., 1984, pp. 553-560) qui décrit des pyranozofurines et ses dérivés ; et - Clingerman et al. (J. Org. Chem. 1983, 48, pp. 3141-3146) qui décrit des dérivés de ribofuranosyle.

Allevi and ai (J. Chem Soc., Chem., 1987, pp. 101-102) which discloses C-glucopyranosyl derivatives; - Nakamura et al. (Tetrahedron Letters, 1996, 37, pp. 3153-3156); Tsang and ai (J. Org Chem 1985, 50, pp. 4659-4661) describes bicyclic pyranose derivatives; - Lay et al. (J. Chem Soc., Perkin Trans 1., 1994, pp. 333-338) which discloses disaccharide derivatives;

- Karagiri et al. (J. Chem Soc., Perkin Trans 1., 1984, pp. 553-560) which describes pyranozofurins and its derivatives; and - Clingerman et al. (J. Org Chem 1983, 48, pp. 3141-3146) which describes ribofuranosyl derivatives.

Whatever the C-glycoside derivatives described in the prior art, the latter have hydroxyl functions that are still protected. These known products are prepared by particularly laborious synthetic methods since they require in all cases to protect the hydroxyl functions.

To the plaintiff's knowledge, only one document published on the Internet on October 2, 2000 (http://www.rsc.org/is/journals/currenUchemcomm/cccon.htm) describes C-glycoside derivatives with unprotected hydroxyl functions. .

The C-glycoside derivatives described in this document are: 3 '- (ss-D-Glucopyranosyl) -propan-2'-one, - 3' - (PD-Mannopyranosyl) -propan-2-one, and - 3'- (D-Glucopyranosyl- (1-> 4) -ss-D-Glucopyranosyl) -propan-2'-one.

These three C-glycoside derivatives are obtained quantitatively in alkaline aqueous medium by condensation of pentane-2,4-dione with respectively D-Glucose, D-Mannose or D-Cellobiose. the Applicant has now discovered new C-glycoside derivatives, easily accessible from a synthetic point of view by the implementation in particular of a method described in the aforementioned document published on the internet or a modified method of this reference.

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Ainsi, l'invention a pour premier objet de nouveaux dérivés C-glycoside répondant à la formule (1) suivante :

dans laquelle, S représente un monosaccharide ou un polysaccharide jusqu'à 20 unités sucre, sous forme pyranose et/ou furanose et de série L et/ou D, ledit mono- ou polysaccharide présentant au moins une fonction hydroxyle obligatoirement libre et/ou éventuellement une ou plusieurs fonction amine éventuellement protégée ; la liaison S-CH2-X représente une liaison de nature C-anomèrique ; - X représente un groupement choisi parmi :-CO-,-CH (OH)-,-CH (NRiR2)-, - CHR'-,-C (=CHR')- ; - R représente une chaîne alkyle, arylalkyl, perfluoroalkyle, hydrofluoroalkyle linéaire ou ramifiée, saturée ou insaturée, un cycle cycloalkyl, cycloperfluoroalkyle, cyclohydrofluoroalkyle, aryle, comprenant de 5 à 28 atomes de carbone, la dite chaîne et/ou ledit cycle pouvant être éventuellement interrompu par un ou plusieurs hétéroatomes choisi parmi l'oxygène, le souffre, l'azote, le silicium, et éventuellement substituée par au moins un radical choisi parmi -OR'1,-SR"1,-NR'''1R'2,-COOR''2, -CONHR'''2, - CN, halogène, perfluoroalkyle, hydrofluoroalkyle et/ou au moins un radical cycloalkyl, aryle, hétérocyclique éventuellement substitués ; - R'représente un hydrogène, une chaîne alkyle, arylalkyl, perfluoroalkyle, hydrofluoroalkyle linéaire ou ramifiée, saturée ou insaturée, un cycle cycloalkyl, cyclope rfluoroalkyle, cyclohydrofluoroalkyle, aryle, comprenant de
1 à 28 atomes de carbone, la dite chaîne ou ledit cycle pouvant être éventuellement interrompu par un ou plusieurs hétéroatomes choisi parmi

Thus, the invention firstly relates to novel C-glycoside derivatives corresponding to the following formula (1):

in which, S represents a monosaccharide or a polysaccharide of up to 20 sugar units, in pyranose and / or furanose form and of L and / or D series, said mono- or polysaccharide having at least one hydroxyl function which is necessarily free and / or possibly one or more amine function optionally protected; the S-CH2-X bond represents a C-anomeric bond; X represents a group chosen from: -CO-, -CH (OH) -, -CH (NRiR2) -, - CHR '-, - C (= CHR') -; R represents an alkyl, arylalkyl, perfluoroalkyl, linear or branched hydrofluoroalkyl, saturated or unsaturated chain, a cycloalkyl, cycloperfluoroalkyl, cyclohydrofluoroalkyl or aryl ring, comprising from 5 to 28 carbon atoms, the said chain and / or said ring being optionally interrupted by one or more heteroatoms selected from oxygen, sulfur, nitrogen, silicon, and optionally substituted by at least one radical selected from -OR'1, -SR "1, -NR '''1R'2 , -COOR''2, -CONHR '''2, - CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical: R' is hydrogen, alkyl chain, arylalkyl, perfluoroalkyl, linear or branched hydrofluoroalkyl, saturated or unsaturated, a cycloalkyl, cyclophaluoroalkyl, cyclohydrofluoroalkyl, aryl ring, comprising
1 to 28 carbon atoms, said chain or said ring possibly being interrupted by one or more heteroatoms chosen from

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l'oxygène, le souffre, l'azote, le silicium, et éventuellement substituée par au moins un radical choisi parmi-OR'i,-SR"1,-NR''iR'2,-COOR"2,-CONHR"'2, - CN, halogène, perfluoroalkyle, hydrofluoroalkyle et/ou au moins un radical cycloalkyl, aryle, hétérocyclique éventuellement substitués ; - Ri, R2, R'i, R'2, R"1, R"2, R'"i, R"'2, identiques ou différents, représentent un atome d'hydrogène, un hydroxyle, un radical choisi parmi un radical alkyle, perfluoroalkyle et/ou hydrofluoroalkyle, linéaire ou ramifié, saturé ou insaturé, comprenant de 1 à 30 atomes de carbone.

oxygen, sulfur, nitrogen, silicon, and optionally substituted by at least one radical chosen from -OR'i, -SR "1, -NR''R'2, -COOR" 2, -CONHR " CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical: R 1, R 2, R '1, R' 2, R "1, R" 2, R '" i, R "'2, which may be identical or different, represent a hydrogen atom, a hydroxyl, a radical chosen from a saturated or unsaturated, linear or branched, saturated or unsaturated alkyl, perfluoroalkyl and / or hydrofluoroalkyl radical comprising from 1 to 30 carbon atoms, carbon.

The invention also relates to the optical and geometric isomers of C-glycoside derivatives corresponding to formula (1), alone or as a mixture, in all proportions, as well as the physiologically acceptable salts of these derivatives.

Physiologically acceptable salts of the derivatives of formula (1) include salts compatible with the skin, the mucous membranes, the nails, the scalp and / or the hair.

The C-anomeric bond can be a or p.

According to the invention, the C-glycoside derivatives corresponding to the formula (1) can be of natural or synthetic origin, totally or partially purified or any preparation containing them.

By natural origin is meant a derivative extracted from natural material in which it is present, for example plants. By synthetic origin is meant a derivative prepared by chemical synthesis or biotechnology.

 The expression "totally or partially purified" means here that, during its synthesis or in relation to its natural state (plant or fresh or dried cells), the C-glycoside derivative corresponding to formula (1) in the composition of the the invention has been concentrated and / or has been stripped, respectively, of at least a part of the secondary reaction products resulting from its synthesis or from

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moins une partie des autres constituants du matériel naturel dans lequel il se trouve présent.

least part of the other constituents of the natural material in which it is present.

le D-galactose, le D-mannose, le D-xylose, le D-lyxose, la N-acétyl-Dglucosamin, le L-fucose, L-arabinose, le L-rhamnose, et représente avantageusement le D-glucose, le D-xylose, la N-acétyl-D-glucosamine, L-fucose et très préférentiellement le D-glucose, Avantageusement encore, les polysaccharides contenant jusqu'à 6 unités sucre sont choisis parmi le D-maltotriose, le D-maltose, le D-lactose, le D-cellobiose et représente avantageusement un disaccharide choisi parmi le D-maltose, le Dlactose, le D-cellobiose, Selon une autre forme préférée de l'invention, on utilise des dérivés C-glycosides répondant à la formule (1) pour lesquels X représente un groupement choisi parmi - CO-,-CH (OH)-,-CH (NRiR2)-,-CH2-,-C (=CHR')- et représente très avantageusement un groupement-CO-ou-CH (OH)-, S et R conservant par ailleurs l'ensemble des définitions précédemment données. According to a preferred form of the invention, C-glycoside derivatives corresponding to formula (1) are used, for which S represents a monosaccharide or a polysaccharide containing up to 6 sugar units, in the form of pyranose and / or furanose, and in series. L and / or D, said mono-or polysaccharide having at least one hydroxyl function necessarily free and optionally one or more optionally protected amine function, Advantageously, the preferred monosaccharides are chosen from D-glucose,

D-galactose, D-mannose, D-xylose, D-lyxose, N-acetyl-Dglucosamin, L-fucose, L-arabinose, L-rhamnose, and is advantageously D-glucose, D-xylose, N-acetyl-D-glucosamine, L-fucose and very preferably D-glucose. Advantageously, the polysaccharides containing up to 6 sugar units are chosen from D-maltotriose, D-maltose, D-lactose, D-cellobiose and advantageously represents a disaccharide chosen from D-maltose, Dlactose, D-cellobiose. According to another preferred form of the invention, C-glycoside derivatives having the formula 1) for which X represents a group chosen from - CO -, - CH (OH) -, - CH (NRiR2) -, - CH2 -, - C (= CHR ') - and very advantageously represents a group -CO- or -CH (OH) -, S and R retaining all the definitions previously given.

In these preferred forms of the invention, C-glycoside derivatives corresponding to formula (1) are used for which R, R ', R 1, R 2, R' 1, R '2, R "R" 2, R " i, R '"2 being defined as above, S and X also retaining all the previously given definitions.

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Parmi les dérivés C-glycoside répondant à la formule (1), on préfère tout particulièrement : - 1-désoxy, 1- (2'-oxo) heptyl-p-D-cellobiose ; - 1-désoxy, 1- (2'-oxo) heptyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo) octyf-p-D-ce ! ! obiose ; - 1-désoxy, 1- (2'-oxo) octyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo) décyl-p-D-cellobiose ; 1-désoxy, 1- (2'-oxo) décyl-a-D-cellobiose - 1-désoxy, 1- (2'-oxo) tétradécyf- (3-D-ce ! ! obiose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo) hexadécyt-) 3-D-cet) obiose ; - 1-désoxy, 1- (2'-oxo) hexadécyi-a-D-ceitobiose ; - 1-désoxy, 1- (2'-oxo) octadécyl-p-D-cet) obiose ; - 1-désoxy, 1- (2'-oxo) octadécyf-a-D-ce ! tobiose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-p-D-cellobiose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-ss-D-cellobiose ; 1-désoxy, 1- (2'-oxo- 10, 1 3-d iène) nonadécyl-a-D-cel lob iose - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-ss-Dcellobiose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Dcellobiose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-3'-trif) uorométhyt-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-p-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo-2'-phény < ) éthyi-p-D-cetiobiose ;

Among the C-glycoside derivatives corresponding to formula (1), the following are particularly preferred: 1-deoxy, 1- (2'-oxo) heptyl-pD-cellobiose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-cellobiose; - 1-deoxy, 1- (2'-oxo) octyf-pD-ce! ! obiose; 1-deoxy, 1- (2'-oxo) octyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo) decyl-pD-cellobiose; 1-deoxy, 1- (2'-oxo) decyl-α-D-cellobiose-1-deoxy, 1- (2'-oxo) tetradecyl- (3-D-1-yl), 1-deoxy, 1- 2'-oxo) tetradecyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo) hexadecyl-) 3-D-cetiobiosis; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-ceitobiosis; 1-deoxy, 1- (2'-oxo) octadecyl-pD-cet) obiosis; 1-deoxy, 1- (2'-oxo) octadecyl-α-D! tobiose; 1-deoxy, 1- (2'-oxo) nonadecyl-pD-cellobiose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-pD-cellobiose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-s-D-cellobiose; 1-Deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-cellobut-1-deoxy, 1- (2'-oxo-3 ', 3', 5 ') ', 6', 6 ', 8', 8 ', 8'-nonafluoro-4', 7'-dioxa) octyl-ss-Dcellobiose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dcellobiose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-cellobiose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl) 3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl -aD-cellobiose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-pD-cellobiose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-pD-cetiobiosis;

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- 1-désoxy, 1- (2'-oxo-2'-phény !) éthy)-a-D-cettobiose ; - 1-désoxy, 1- (2'-oxo-2'-phény !-o-hydroxyphény !) éthyt-P-D-ce !) obiose ; - 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-amino) heptyl-p-D-cellobiose ; 1-désoxy, 1- (2'-amino) heptyl-a-D-cellobiose - 1-désoxy, 1- (2'-hydroxy) heptyl-p-D-cellobiose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-a-D-cellobiose ; - 1-désoxy, 1- (2'-oxo) heptyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo) hepty !-a-D-gtucose ; - 1-désoxy, 1- (2'-oxo) octyl-ss-D-glucose ; - 1-désoxy, 1- (2'-oxo) octyt-a-D-g ! ucose ; - 1-désoxy, 1- (2'-oxo) décyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo) décyt-a-D-gtucose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-a-D-glucose ; - 1-désoxy, 1- (2'-oxo) hexadécyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo) hexadécyl-a-D-glucose ; - 1-désoxy, 1- (2'-oxo) octadécyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo) octadécy < -a-D-g ! ucose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo) nonadécy !-a-D-g ! ucose ; 1-désoxy, l- (2'-oxo-10'-ène) nonadécyl-0-D-glucose - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-D-glucose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo-10, 13-d ! ène) nonadécy !-a-D-g) ucose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-ss-Dglucose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Dglucose ; - 1-désoxy, 1- (2'-oxo-3'-trif) uorométhyf-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-D-glucose ;

1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl) -α-D-cobibose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-p-p-benzol); obiosis; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-α-D-cellobiose; 1-deoxy, 1- (2'-amino) heptyl-pD-cellobiose; 1-deoxy, 1- (2'-amino) heptyl-α-D-cellobiose-1-deoxy, 1- (2'-hydroxy) heptyl-pD-cellobiose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo) heptyl-β-glucose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-glucoside; 1-deoxy, 1- (2'-oxo) octyl-ss-D-glucose; 1-deoxy, 1- (2'-oxo) octyl-αDg! ucose; 1-deoxy, 1- (2'-oxo) decyl-β-glucose; 1-deoxy, 1- (2'-oxo) decyt-α-D-glucoside; 1-deoxy, 1- (2'-oxo) tetradecyl-pD-glucose; 1-deoxy, 1- (2'-oxo) tetradecyl-α-D-glucose; 1-deoxy, 1- (2'-oxo) hexadecyl-β-glucose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-glucose; 1-deoxy, 1- (2'-oxo) octadecyl-β-glucose; 1-deoxy, 1- (2'-oxo) octadecyl-α-Dg! ucose; 1-deoxy, 1- (2'-oxo) nonadecyl-β-glucose; - 1-deoxy, 1- (2'-oxo) nonadecyl! -ADg! ucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-O-D-glucose-1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-glucose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-β-glucose; 1-deoxy, 1- (2'-oxo-10,13-dienene) nonadecyl-α-Dg) ucose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Dglucose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dglucose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl) 3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl -ss-D-glucose;

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1-désoxy, 1- (2-oxo-3'-trifl uorométhyl-3', 5', 5', 6', 6', 7', T, T, 7'-octafluoro- 4') oxaheptyl-a-D-glucose ; 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-p-D-glucose - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-a-D-glucose ; - 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-p-D-glucose ; - 1-désoxy, 1- (2'-oxo-2'-phényt) éthyt-a-D-g ! ucose ; 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-p-D-glucose - 1-désoxy, 1- (2'-oxo-2'-phény)-o-hydroxyphény !) éthy !-a-D-g ! ucose ; - 1-désoxy, 1- (2'-amino) heptyl-p-D-glucose ; - 1-désoxy, 1- (2'-amino) heptyl-a-D-glucose ; - 1-désoxy, 1- (2'-hydroxy) hepty !- (3-D-g) ucose ; - 1-désoxy, 1- (2'-hydroxy) hepty < -a-D-g ! ucose ; - 1-désoxy, 1- (2'-oxo) heptyl-p-D-maltose ; - 1-désoxy, 1- (2'-oxo) heptyt-a-D-ma) tose ; - 1-désoxy, 1- (2'-oxo) octyl-p-D-maltose ; - 1-désoxy, 1- (2'-oxo) octy)-a-D-ma) tose ; - 1-désoxy, 1- (2'-oxo) décyl-p-D-maltose ; - 1-désoxy, 1- (2'-oxo) décy)-a-D-ma) tose ; - 1-désoxy, 1- (2'-oxo) tétradécy)- (3-D-ma < tose ; - 1-désoxy, 1- (2'-oxo) tétradécyJ-a-D-ma < tose ; - 1-désoxy, 1- (2'-oxo) hexadécyl-p-D-maltose ; - 1-désoxy, 1- (2'-oxo) hexadécyt-a-D-ma) tose ; - 1-désoxy, 1- (2'-oxo) octadécy)-) 3-D-ma ! tose ; - 1-désoxy, 1- (2'-oxo) octadécyl-a-D-maltose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-p-D-maltose ; - 1-désoxy, 1- (2'-oxo) nonadécy !-a-D-ma ! tose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-D-maltose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyt-a-D-ma ! tose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-ss-D-maltose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-D-maltose ; 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6, 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-p-12maltose ;

1-Deoxy, 1- (2-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', T, T, 7'-octafluoro-4 ') oxaheptyl-aD -glucose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-pD-glucose-1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-D-glucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-pD-glucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-Dg! ucose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-glucose-1-deoxy, 1- (2'-oxo-2'-phenyl) -o-hydroxyphenyl) Ethy! -aDg! ucose; 1-deoxy, 1- (2'-amino) heptyl-pD-glucose; 1-deoxy, 1- (2'-amino) heptyl-α-D-glucose; 1-deoxy, 1- (2'-hydroxy) heptyl, (3-Dg) ucose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-Dg! ucose; 1-deoxy, 1- (2'-oxo) heptyl-pD-maltose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-ma) tose; 1-deoxy, 1- (2'-oxo) octyl-pD-maltose; 1-deoxy, 1- (2'-oxo) octy) -α-D-ma) tose; 1-deoxy, 1- (2'-oxo) decyl-β-maltose; 1-deoxy, 1- (2'-oxo) decyl) -α-D-methyl; 1-deoxy, 1- (2'-oxo) tetradecyl) - (3-D-methyl) -1-deoxy, 1- (2'-oxo) tetradecyl-α-D-methyl-1-deoxy; 1- (2'-oxo) hexadecyl-pD-maltose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-methyl); - 1-deoxy, 1- (2'-oxo) octadecyl) -) 3-D-ma! tose; 1-deoxy, 1- (2'-oxo) octadecyl-α-maltose; 1-deoxy, 1- (2'-oxo) nonadecyl-pD-maltose; - 1-deoxy, 1- (2'-oxo) nonadecyl! -AD-ma! tose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-pD-maltose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-ma! tose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-s-D-maltose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-maltose; 1-deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6, 8', 8 ', 8'-nonafluoro-4', 7'-dioxa) octyl-p -12maltose;

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- 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Dmaltose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-D-maltose ; 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5, 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-D-maltose ; - 1-désoxy, 1- (2'-oxo-2'-undecaftuorocyc) ohexyt) éthy)-p-D-mattose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-a-D-maltose ; - 1-désoxy, 1- (2'-oxo-2'-phény < ) éthyi- (3-D-maftose ; - 1-désoxy, 1- (2'-oxo-2'-phény)) éthyt-a-D-mattose ; - 1-désoxy, 1- (2'-oxo-2'-phényt-o-hydroxyphényt) éthyt- (3-D-mattose ; - 1-désoxy, 1- (2'-oxo-2'-phény !-o-hydroxyphény)) éthy !-a-D-ma ! tose ; - 1-désoxy, 1- (2'-amino) hepty)-p-D-ma ! tose ; - 1-désoxy, 1- (2'-amino) heptyt-a-D-ma) tose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-p-D-maltose ; - 1-désoxy, 1- (2'-hydroxy) heptyt-a-D-ma ! tose ; - 1-désoxy, 1- (2'-oxo) heptyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo) hepty (-a-D-tactose ; - 1-désoxy, 1- (2'-oxo) octyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo) octy !-a-D-) actose ; - 1-désoxy, 1- (2'-oxo) décy)- (3-D-iactose ; - 1-désoxy, 1- (2'-oxo) décyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-p-D-lactose ; 1-désoxy, 1- (2'-oxo) tétradécyl- (x-D-lactose - 1-désoxy, 1- (2'-oxo) hexadécyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo) hexadécyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo) octadécyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo) octadécyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo) nonadécy (-a-D- ! actose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-D-lactose ;

1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dmaltose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-maltose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5, 6 ', 6', 7 ', 7', 7'-octafluoro (4 ') oxaheptyl-α-maltose ; 1-deoxy, 1- (2'-oxo-2'-undecaftuorocyclohexyl) ethyl) -pD-mattose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-D-maltose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl- (3-D-maftose) -1-deoxy, 1- (2'-oxo-2'-phenyl) ethyt-aD -mattose; 1-Deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl- (3-D-mattose) -1-deoxy, 1- (2'-oxo-2'-phenyl) -1- o-hydroxyphenyl)) ethy! -aD-ma! tose; - 1-deoxy, 1- (2'-amino) heptyl) -pD-ma! tose; 1-deoxy, 1- (2'-amino) heptyl-α-D-ma) tose; 1-deoxy, 1- (2'-hydroxy) heptyl-pD-maltose; - 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-ma! tose; 1-deoxy, 1- (2'-oxo) heptyl-β-lactose; 1-desoxy, 1- (2'-oxo) heptyl-α-D-lactose, 1-deoxy, 1- (2'-oxo) octyl-D-lactose, 1-deoxy, 1- oxo) octy! -aD-) actose; 1-deoxy, 1- (2'-oxo) decyl) - (3-D-lactose) -1-deoxy, 1- (2'-oxo) decyl-α-lactose, -1-deoxy, 1- ( 2'-oxo) tetradecyl-β-lactose, 1-deoxy, 1- (2'-oxo) tetradecyl- (x-D-lactose-1-deoxy, 1- (2'-oxo) hexadecyl-β-lactose; deoxy, 1- (2'-oxo) hexadecyl-α-lactose; 1-deoxy, 1- (2'-oxo) octadecyl-β-lactose; 1-deoxy, 1- (2'-oxo) octadecyl; α-lactose, 1-deoxy, 1- (2'-oxo) nonadecyl-β-lactose, 1-deoxy, 1- (2'-oxo) nonadecyl (α-D-actose) -1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-β-lactose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-lactose;

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- 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-p-Dlactose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-D lactose ; - 1-désoxy, 1- (2'-oxo-3'-trif ! uorométhyi-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-D-lactose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-p-D-lactose ; - 1-désoxy, 1- (2'-oxo-2'-phény !) éthy !-a-D-iactose ; - 1-désoxy, 1- (2'-oxo-2'-phény)-o-hydroxyphény)) éthy !-p-D-tactose ; - 1-désoxy, 1- (2'-oxo-2'-phény)-o-hydroxyphényt) éthy !-a-D-) actose ; - 1-désoxy, 1- (2'-amino) hepty)- (3-D-tactose ; - 1-désoxy, 1- (2'-amino) hepty)-a-D-) actose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-p-D-lactose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-a-D-lactose ; - 1-désoxy, 1- (2'-oxo) heptyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo) hepty)-a-N-acéty)-D-g) ucosamine ; 1-désoxy, 1- (2'-oxo) octyl-p-N-acétyl-D-glucosamine - 1-désoxy, 1- (2'-oxo) octy < -a-N-acéty !-D-gfucosamine ; 1-désoxy, l- (2'-oxo) décyl-p-N-acétyl-D-glucosamine - 1-désoxy, 1- (2'-oxo) décy !-a-N-acéty < -D-g < ucosamine ; - 1-désoxy, 1- (2'-oxo) tétradécy !- (3-N-acéty)-D-g (ucosamine ; - 1-désoxy, 1- (2'-oxo) tétradécy !-a-N-acéty !-D-g) ucosamine ; 1-désoxy, l- (2'-oxo) hexadécyl-p-N-acétyl-D-glucosamine - 1-désoxy, 1- (2'-oxo) hexadécyt-a-N-acétyt-D-g) ucosamine ; - 1-désoxy, 1- (2'-oxo) octadécyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo) octadécy !-a-N-acétyi-D-gtucosamine ;

1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-β-lactose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-lactose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -p-Dlactose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl lactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl) -ss-D-lactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD lactose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-pD-lactose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-lactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-β-lactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-lactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) -o-hydroxyphenyl) ethyl-pD-tactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) -o-hydroxyphenyl) ethyl-α-D-actose; 1-deoxy, 1- (2'-amino) heptyl) - (3-D-tactose) -1-deoxy, 1- (2'-amino) heptyl) -α-) actose; 1-deoxy, 1- (2'-hydroxy) heptyl-β-lactose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-lactose; 1-deoxy, 1- (2'-oxo) heptyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) heptyl) -N-acetyl) -DG) ucosamine; 1-deoxy, 1- (2'-oxo) octyl-pN-acetyl-D-glucosamine-1-deoxy, 1- (2'-oxo) octyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) decyl-pN-acetyl-D-glucosamine-1-deoxy, 1- (2'-oxo) decyl-N-acetyl-α-glucosamine; 1-desoxy, 1- (2'-oxo) tetradecyl- (3-N-acetyl) -Dg (ucosamine) -1-deoxy, 1- (2'-oxo) tetradecyl-N-acetyl-dg ucosamine; 1-deoxy, 1- (2'-oxo) hexadecyl-pN-acetyl-D-glucosamine-1-deoxy, 1- (2'-oxo) hexadecyl-N-acetyl-D8) ucosamine; 1-deoxy, 1- (2'-oxo) octadecyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) octadecyl-N-acetyl-D-glucosamine;

<Desc / Clms Page number 12>

- 1-désoxy, 1- (2'-oxo) nonadécyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo) nonadécy !-a-N-acéty !-D-g < ucosamine ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-p-Nacétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Nacétyl-D-glucosamine ; 1-désoxy, 1- (2-oxo-3'-trifluorométhyl-3, 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-N-acétyl-D-glucosamine ; 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-p-N-acétyl-D glucosamin ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-a-N-acétyl-Dglucosamin ; 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-oxo-2'-phényt) éthyt-a-N-acéty !-D-g < ucosamine ; 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-p-N-acétyl-Dglucosamin ; - 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-a-N-acétyl-Dglucosamin ; 1-désoxy, 1- (2'-amino) heptyl-p-N-acétyl-D-glucosamine - 1-désoxy, 1- (2'-amino) hepty !-a-N-acétyt-D-gfucosamine ; - 1-désoxy, 1- (2'-hydroxy) heptyl-p-N-acétyl-D-glucosamine ; - 1-désoxy, 1- (2'-hydroxy) hepty)-a-N-acéty !-D-gfucosamine ; - 1-désoxy, 1- (2'-oxo) heptyl-p-D-xylose ; - 1-désoxy, 1- (2'-oxo) heptyl-a-D-xylose ; - 1-désoxy, 1- (2'-oxo) octyl-p-D-xylose ; - 1-désoxy, 1- (2'-oxo) octyl-a-D-xylose ;

1-deoxy, 1- (2'-oxo) nonadecyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) nonadecyl-α-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-N-acetyl-D-glucosamine; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl p-Nacetyl-D-glucosamine; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl α-N-acetyl-D-glucosamine; 1-Deoxy, 1- (2-oxo-3'-trifluoromethyl-3,5 ', 5', 6 ', 6', 7 ', 7', 7'-octafluoro (4 ') oxaheptyl-ss-N- acetyl-D-glucosamine; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aN acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-pN-acetyl-D glucosamin; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pN-acetyl-Dglucosamin; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-amino) heptyl-pN-acetyl-D-glucosamine-1-deoxy, 1- (2'-amino) heptyl-α-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-hydroxy) heptyl-pN-acetyl-D-glucosamine; 1-deoxy, 1- (2'-hydroxy) heptyl) -N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) heptyl-pD-xylose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-xylose; 1-deoxy, 1- (2'-oxo) octyl-pD-xylose; 1-deoxy, 1- (2'-oxo) octyl-α-D-xylose;

<Desc / Clms Page number 13>

- 1-désoxy, 1- (2'-oxo) décyl-p-D-xylose ; - 1-désoxy, 1- (2'-oxo) décyl-a-D-xylose ; 1-désoxy, 1- (2'-oxo) tétradécyl-p-D-xyl ose - 1-désoxy, 1- (2'-oxo) tétradécy)-a-D-xytose ; - 1-désoxy, 1- (2'-oxo) hexadécy)-p-D-xy ! ose ; 1-désoxy, 1- (2'-oxo) hexadécyl-a-D-xylose - 1-désoxy, 1- (2'-oxo) octadécyt- (3-D-xy) ose ; - 1-désoxy, 1- (2'-oxo) octadécyt-a-D-xy < ose ; - 1-désoxy, 1- (2'-oxo) nonadécy)- (3-D-xytose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-a-D-xylose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-D-xylose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-D-xylose ; 1-désoxy, l- (2-oxo-10, 13-diène) nonadécyl-p-D-xylose - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-D-xylose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-ss-Dxylose ; 1-dés oxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Dxylose ; - 1-désoxy, 1- (2'-oxo-3'-trif) uorométhy !-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-D-xylose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-D-xylose ; - 1-désoxy, 1- (2'-oxo-2'-undecaftuorocyctohexy < ) éthy !-j3-D-xybse ; - 1-désoxy, 1- (2'-oxo-2'-undecaf ! uorocydohexy)) éthy)-a-D-xy) ose ; - 1-désoxy, 1- (2'-oxo-2'-phény !) éthy !-j3-D-xy) ose ; - 1-désoxy, 1- (2'-oxo-2'-phény)) éthyt-a-D-xy ! ose ; - 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-p-D-xylose ; - 1-désoxy, 1- (2'-oxo-2'-phényt-o-hydroxyphény () éthy)-a-D-xy ! ose ; - 1-désoxy, 1- (2'-amino) heptyl-p-D-xylose ; - 1-désoxy, 1- (2'-amino) heptyl-a-D-xylose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-p-D-xylose ; - 1-désoxy, 1- (2'-hydroxy) hepty !-a-D-xytose ;

1-deoxy, 1- (2'-oxo) decyl-pD-xylose; 1-deoxy, 1- (2'-oxo) decyl-α-D-xylose; 1-deoxy, 1- (2'-oxo) tetradecyl-pD-xylose-1-deoxy, 1- (2'-oxo) tetradecyl) -α-xytose; - 1-deoxy, 1- (2'-oxo) hexadecyl) -pD-xy! dare; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-xylose-1-deoxy, 1- (2'-oxo) octadecyl- (3-D-xyl) -ose; 1-deoxy, 1- (2'-oxo) octadecyl-α-xylose; 1-desoxy, 1- (2'-oxo) nonadecyl) - (3-D-xylose) -1-deoxy, 1- (2'-oxo) nonadecyl-α-D-xylose, 1-deoxy, 1- ( 2'-oxo-10'-ene) nonadecyl-pD-xylose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-xylose; 1-deoxy, 1- (2-oxo); 10, 13-diene) nonadecyl-pD-xylose-1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-xylose; 1-deoxy, 1- (2'-oxo), 3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl-s-dxylose; 1-desoxy, 1- ( 2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl-α-hexylose; deoxy, 1- (2'-oxo-3'-trifluoromethyl) -3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl-ss -D-xylose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD xylose; 1-deoxy, 1- (2'-oxo-2'-undecaftuorocyclohexyl) ethyl-3-D-xylase; 1-deoxy, 1- (2'-oxo-2'-undecafluorocydohexy)) ethyl) -α-xyloseose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-3-D-xyloseose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-xyl! dare; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-xylose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl) -α-xyl dare; 1-deoxy, 1- (2'-amino) heptyl-pD-xylose; 1-deoxy, 1- (2'-amino) heptyl-α-D-xylose; 1-deoxy, 1- (2'-hydroxy) heptyl-pD-xylose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-dimethyl;

<Desc / Clms Page number 14>

- 1-désoxy, 1- (2'-oxo) hepty !-f3-L-fucose ; - 1-désoxy, 1- (2'-oxo) heptyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo) octy !-p-L-fucose ; - 1-désoxy, 1- (2'-oxo) octyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo) décy !- (3-L-fucose ; - 1-désoxy, 1- (2'-oxo) décyl-a-L-fucose ; 1-désoxy, 1- (2'-oxo) tétradécyl-p-L-fucose - 1-désoxy, 1- (2'-oxo) tétradécyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo) hexadécyf-p-L-fucose ; - 1-désoxy, 1- (2'-oxo) hexadécyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo) octadécy !-p-L-fucose ; - 1-désoxy, 1- (2'-oxo) octadécyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo) nonadécy)-p-L-fucose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-ss-L-fucose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-ss-L-fucose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-ss-Lfucose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Lfucose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-L-fucose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-p-L-fucose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-p-L-fucose ; - 1-désoxy, 1- (2'-oxo-2'-phény < ) éthy)-a-L-fucose ; 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-p-L-fucose - 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-a-L-fucose ;

1-deoxy, 1- (2'-oxo) heptyl-β-L-fucose; 1-deoxy, 1- (2'-oxo) heptyl-α-Fucose; 1-deoxy, 1- (2'-oxo) octyl-pL-fucose; 1-deoxy, 1- (2'-oxo) octyl-α-Fucose; 1-desoxy, 1- (2'-oxo) decyl, (3-L-fucose) -1-deoxy, 1- (2'-oxo) decyl-α-fucose, 1-deoxy, 1- tetradecyl-pL-fucose-1-deoxy, 1- (2'-oxo) tetradecyl-α-fucose, 1-deoxy, 1- (2'-oxo) hexadecyl-pL-fucose; deoxy, 1- (2'-oxo) hexadecyl-α-fucose, 1-deoxy, 1- (2'-oxo) octadecyl-pL-fucose, 1-deoxy, 1- (2'-oxo) octadecyl, α-fucose, 1-deoxy, 1- (2'-oxo) nonadecyl-β-fucose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-fucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-s-L-fucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-Fucose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-s-L-fucose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-fucose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Lfucose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -Flucose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss L-fucose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aL -fucose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-pL-fucose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-fucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-pL-fucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl) -L-fucose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pL-fucose-1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl- aL-fucose;

<Desc / Clms Page number 15>

- 1-désoxy, 1- (2'-amino) heptyl-ss-L-fucose ; - 1-désoxy, 1- (2'-amino) heptyl-a-L-fucose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-ss-L-fucose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-a-L-fucose ; - 1-désoxy, 1- (2'-oxo) hepty !-) 3-D-mannose ; - 1-désoxy, 1- (2'-oxo) heptyl-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) octy)-p-D-mannose ; - 1-désoxy, 1- (2'-oxo) octyt-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) décy !-p-D-mannose ; - 1-désoxy, 1- (2'-oxo) décyt-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-p-D-mannose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) hexadécy)-j3-D-mannose ; - 1-désoxy, 1- (2'-oxo) hexadécyt-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) octadécyl-p-D-mannose ; - 1-désoxy, 1- (2'-oxo) octadécy)-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) nonadécyt- (3-D-mannose ; - 1-désoxy, 1- (2'-oxo) nonadécy !-a-D-mannose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-D-mannose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyt-a-D-rnannose ; 1-désoxy, l- (2'-oxo-10, 13-diène) nonadécyl-p-D-mannose - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-D-mannose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-ss-Dmannose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafiuoro-4', 7'-dioxa) octyl-a-Dmannose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7-octafluor- 4') oxaheptyl-ss-D-mannose ; 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-D-mannose ; - 1-désoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) éthyl-p-D-mannose ; - 1-désoxy, 1- (2'-oxo-2'-undecaftuorocydohexyt) éthy !-a-D-mannose ;

1-deoxy, 1- (2'-amino) heptyl-s-L-fucose; 1-deoxy, 1- (2'-amino) heptyl-α-fucose; 1-deoxy, 1- (2'-hydroxy) heptyl-ss-L-fucose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-fucose; 1-deoxy, 1- (2'-oxo) heptyl-3-D-mannose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) octy) -pD-mannose; 1-deoxy, 1- (2'-oxo) octyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) decyl-pD-mannose; 1-deoxy, 1- (2'-oxo) decyt-α-D-mannose; 1-deoxy, 1- (2'-oxo) tetradecyl-pD-mannose; 1-deoxy, 1- (2'-oxo) tetradecyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) hexadecyl) -3-D-mannose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) octadecyl-pD-mannose; - 1-deoxy, 1- (2'-oxo) octadecyl) -α-mannose; 1-desoxy, 1- (2'-oxo) nonadecyl- (3-D-mannose) -1-deoxy, 1- (2'-oxo) nonadecyl-α-D-mannose, 1-deoxy, 1- ( 2'-oxo-10'-ene) nonadecyl-pD-mannose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-mannose; 1-deoxy, 1- (2'-oxo-10'-ene); oxo-10,13-diene) nonadecyl-pD-mannose-1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-mannose; 1-deoxy, 1- (2'-oxo); 3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl-s-Dmannose; (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl-a-Dmannose; deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7-octafluoro (4') oxaheptyl-ss-D- mannose, 1-deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl); α-Mannose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-pD-mannose; 1-deoxy, 1- (2'-oxo-2'-undecaftuorocyclohexyt) ethyl-αD; -mannose;

<Desc / Clms Page number 16>

- 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-p-D-mannose ; - 1-désoxy, 1- (2'-oxo-2'-phény !) éthyt-a-D-mannose ; - 1-désoxy, 1- (2'-oxo-2'-phényl-o-hydroxyphényl) éthyl-p-D-mannose ; - 1-désoxy, 1- (2'-oxo-2'-phény !-o-hydroxyphény !) éthy)-a-D-mannose ; - 1-désoxy, 1- (2'-amino) heptyl-p-D-mannose ; - 1-désoxy, 1- (2'-amino) heptyl-a-D-mannose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-p-D-mannose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-a-D-mannose ; - 1-désoxy, 1- (2'-oxo) heptyl-p-D-galactose ; - 1-désoxy, 1- (2'-oxo) hepty < -a-D-gafactose ; - 1-désoxy, 1- (2'-oxo) octyl-p-D-galactose ; - 1-désoxy, 1- (2'-oxo) octy !-a-D-ga) actose ; - 1-désoxy, 1- (2'-oxo) décyl-p-D-galactose ; - 1-désoxy, 1- (2'-oxo) décyt-a-D-gaiactose ; - 1-désoxy, 1- (2'-oxo) tétradécyl-p-D-galactose - 1-désoxy, 1- (2'-oxo) tétradécyt-a-D-gatactose ; - 1-désoxy, 1- (2'-oxo) hexadécyl-p-D-galactose ; - 1-désoxy, 1- (2'-oxo) hexadécy)-a-D-gatactose ; 1-désoxy, 1- (2'-oxo) octadécyl-p-D-galactose - 1-désoxy, 1- (2'-oxo) octadécyt-a-D-ga ! actose ; - 1-désoxy, 1- (2'-oxo) nonadécyl-p-D-galactose ; - 1-désoxy, 1- (2'-oxo) nonadécyt-a-D-ga < actose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-p-D-galactose ; - 1-désoxy, 1- (2'-oxo-10'-ène) nonadécyl-a-D-galactose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-ss-D-galactose ; - 1-désoxy, 1- (2'-oxo-10, 13-diène) nonadécyl-a-D-galactose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-p-Dgalactose ; - 1-désoxy, 1- (2'-oxo-3', 3', 5', 5', 6', 6', 8', 8', 8'nonafluoro-4', 7'-dioxa) octyl-a-Dgalactose ; - 1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-ss-D-galactose ;

1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-pD-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-D-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl) -α-mannose; 1-deoxy, 1- (2'-amino) heptyl-pD-mannose; 1-deoxy, 1- (2'-amino) heptyl-α-D-mannose; 1-deoxy, 1- (2'-hydroxy) heptyl-pD-mannose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) heptyl-β-D-galactose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-gafactose; 1-deoxy, 1- (2'-oxo) octyl-β-D-galactose; 1-deoxy, 1- (2'-oxo) octyl-α-D-ga) actose; 1-deoxy, 1- (2'-oxo) decyl-β-D-galactose; 1-deoxy, 1- (2'-oxo) decyt-α-D-galactose; 1-deoxy, 1- (2'-oxo) tetradecyl-pD-galactose-1-deoxy, 1- (2'-oxo) tetradecyl-α-D-galactose; 1-deoxy, 1- (2'-oxo) hexadecyl-β-D-galactose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-galactose; 1-deoxy, 1- (2'-oxo) octadecyl-β-D-galactose-1-deoxy, 1- (2'-oxo) octadecyl-α-D-gal; actose; 1-deoxy, 1- (2'-oxo) nonadecyl-β-D-galactose; - 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-galactose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-β-D-galactose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-galactose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-s-D-galactose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-galactose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl p -galactose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dgalactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-galactose;

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1-désoxy, 1- (2'-oxo-3'-trifluorométhyl-3', 5', 5', 6', 6', 7', 7', 7'-octafluor- 4') oxaheptyl-a-D-galactose ; - 1-désoxy, 1- (2'-oxo-2'-undecaf) uorocyctohexy)) éthyi-p-D-gatactose ; - 1-désoxy, 1- (2'-oxo-2'-undecaftuorocyctohexyi) éthyt-a-D-gatactose ; - 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-p-D-galactose ; 1-désoxy, 1- (2'-oxo-2'-phényl) éthyl-a-D-galactose - 1-désoxy, 1- (2'-oxo-2'-phényt-o-hydroxyphényt) éthyt-p-D-gatactose ; - 1-désoxy, 1- (2'-oxo-2'-phényt-o-hydroxyphényt) éthyt-a-D-gatactose ; - 1-désoxy, 1- (2'-amino) hepty)- (3-D-gatactose ; - 1-désoxy, 1- (2'-amino) hepty)-a-D-gatactose ; - 1-désoxy, 1- (2'-hydroxy) heptyl-p-D-galactose ; - 1-désoxy, 1- (2'-hydroxy) heptyf-a-D-gatactose.

1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl-α-D- galactose; 1-deoxy, 1- (2'-oxo-2'-undecaf) uorocyctohexy)) ethyl-pD-gatactose; 1-deoxy, 1- (2'-oxo-2'-undecaftuorocyclohexyl) ethyl-α-D-galactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-pD-galactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-D-galactose-1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-gatactose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-α-D-galactose; 1-deoxy, 1- (2'-amino) heptyl) - (3-D-gatactose; 1-deoxy, 1- (2'-amino) heptyl) -α-D-galactose; 1-deoxy, 1- (2'-hydroxy) heptyl-β-D-galactose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-galactose.

Furthermore, the C-glycoside derivatives of formula (1) for which X corresponds to -CO- constitute particularly interesting synthetic intermediates, precisely because of the presence of this -CO-reactive group, which makes it possible to obtain C-derivatives. -Glycoside of formula (1) for which X corresponds to -CH (OH) -, -CH (NR1R2) -, -CHR'-, -C (= CHR ') -, as described below.

The C-glycoside derivatives of formula (1) for which X corresponds to -CO-are obtained in particular by a synthesis method which is an adaptation of that described in the aforementioned document published on the internet.

The formation of C-glycoside derivatives of formula (1) for which X corresponds to -CO- results from the condensation of a ss-diketone on a monosaccharide or a polysaccharide up to 20 sugar units, in pyranose and / or furanose form. and L and / or D series, said mono-or polysaccharide having at least one hydroxyl function necessarily free and / or optionally one or more amine function necessarily protected.

Thus, a second subject of the invention relates to a process for the preparation of the new C-glycoside derivatives corresponding to formula (1) as defined above and for which X corresponds to -CO-, characterized in that it consists of :

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- à dissoudre dans de l'eau ou dans un mélange constitué d'eau et d'un solvant polaire et avantageusement le tétrahydrofuranne, le dioxanne, la N-méthyl- pyrrolidone, le glycérol, le diméthylsulfoxyde, l'acétale d'éthyle, le tert-butyl- méthyl-éther, la pyridine ou l'isopropanol, le diméthylformamide, acétonitrile, le dichlorométhane, et les alcools en particulier l'éthanol, 1 équivalent d'un monosaccharide ou un polysaccharide de formule S tel que défini précédemment, à additionner entre 1 et 5 équivalents d'un composé p- dicétonique de formule générale R"-CO-CH2-CO-R, avec R tel que défini précédemment et R"correspondant à la définition donnée précédemment pour
R', à l'exception de l'hydrogène, et entre 1 et 5 équivalents d'une base organique ou minérale, de préférence minérale et à chauffer le mélange réactionnel à une température comprise entre 40 et 110 cl, de préférence entre 75 et 100 OC, pendant une durée comprise entre 3 et 30h, de préférence entre 5 et 18h, - puis, après refroidissement, à laver le milieu réactionnel avec un solvant

organique pouvant être choisi notamment parmi l'acétate d'éthyle, le dichlorométhane, le diéthylether, le disopropyléther, le terbutylméthyléther, la méthyléthylcétone, - à neutraliser la phase aqueuse par un acide minéral ou organique ou par passage sur une résine acide, - à concentrer puis à co-évaporer avec un solvant organique choisi parmi l'éthanol, le méthanol, le toluène et/ou l'isopropanol, - à sécher sous vide le produit obtenu, puis éventuellement à le purifier par chromatographie et/ou cristallisation.

to dissolve in water or in a mixture consisting of water and a polar solvent and advantageously tetrahydrofuran, dioxane, N-methylpyrrolidone, glycerol, dimethylsulfoxide, ethyl acetal, tert-butyl-methyl-ether, pyridine or isopropanol, dimethylformamide, acetonitrile, dichloromethane, and alcohols, in particular ethanol, 1 equivalent of a monosaccharide or a polysaccharide of formula S as defined above, to add between 1 and 5 equivalents of a p-diketone compound of the general formula R "-CO-CH 2 -CO-R, with R as defined above and R" corresponding to the definition previously given for
R ', with the exception of hydrogen, and between 1 and 5 equivalents of an organic or inorganic base, preferably mineral, and heating the reaction mixture to a temperature of between 40 and 110 cl, preferably between 75 and 100 OC, for a period of between 3 and 30h, preferably between 5 and 18h, and then, after cooling, washing the reaction medium with a solvent

organic compound which may be chosen in particular from ethyl acetate, dichloromethane, diethyl ether, disopropyl ether, terbutyl methyl ether, methyl ethyl ketone, - to neutralize the aqueous phase with an inorganic or organic acid or by passing over an acidic resin, - concentrate and then co-evaporate with an organic solvent selected from ethanol, methanol, toluene and / or isopropanol, - to dry under vacuum the product obtained, then optionally to purify by chromatography and / or crystallization.

A detailed example of preparation of a C-glycoside derivative corresponding to formula (1) as defined above and for which X corresponds to -CO- is given in the examples without limiting the invention.

The synthesis method according to the invention has the advantage of allowing quick and easy access to the new C-glycoside derivatives corresponding to formula (1) as defined above and for which X corresponds to -CO-, because of that they are obtained in a single step using as solvent water or in a

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mélange constitué d'eau et d'un solvant miscible dans l'eau, l'eau ou ledit mélange étant compatibles avec la chimie des sucres présentant des fonctions hydroxyles sous forme libre.

mixture consisting of water and a solvent miscible in water, the water or said mixture being compatible with the chemistry of sugars having hydroxyl functions in free form.

In addition, the yields are excellent.

The C-glycoside derivatives of formula (1) for which X corresponds to -CH (OH) -, - CH (NR 1 R 2) -, - CHR '-, - C (= CHR') - are obtained from C derivatives. glycoside of formula (1) for which X corresponds to -CO-by methods well known to those skilled in the art such as those described in Advanced Organic Chemistry, Reactions, Mechanisms and Structure, Jerry March (IV Edition) 1992.

These methods may possibly require the protection and deprotection of the hydroxyl functions, these methods of protection and deprotection being also well known to those skilled in the art, for example those described in the document Protective Groups in Organic Synthesis, Greene TW, PGM Wuts (Wiley Interscience).

A third subject of the invention also relates to a composition comprising at least one C-glycoside derivative of formula (1) as defined above.

Of course, the composition according to the invention may comprise C-glycoside derivatives corresponding to formula (1) alone or in mixtures and in all proportions.

To give an order of magnitude, the composition of the invention may contain at least one C-glycoside derivative corresponding to formula (1) in an amount representing from 0.1% to 50% of the total weight of the composition and preferably in an amount representing from 0.5% to 20% of the total weight of the composition.

The composition according to the invention may be intended for cosmetic or pharmaceutical use, particularly dermatological use. Preferably, the composition according to the invention is intended for cosmetic use.

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La Demanderesse a découvert de façon inattendue que des dérivés C-glycoside de formule (1) tels que définis précédemment constituent une nouvelle famille d'agents amphiphiles.

The Applicant has unexpectedly discovered that C-glycoside derivatives of formula (1) as defined above constitute a new family of amphiphilic agents.

Thus, the fourth subject of the present invention is the use of at least one C-glycoside derivative corresponding to formula (1) as defined previously as amphiphilic agents.

According to another subject, the invention relates to the use of at least one C-glycoside derivative corresponding to formula (1) as defined above, in a cosmetic and / or dermatological composition comprising a physiologically acceptable medium, such as amphiphilic agents.

The present invention also relates to the use of at least one C-glycoside derivative corresponding to formula (1) as defined above in a cosmetic and / or dermatological composition, as emulsifiers, as surfactants or as agents which can form , lamellar phases, leading to lipid vesicles.

The invention also relates to the optical and / or geometric isomers of C-glycoside derivatives corresponding to formula (1), alone or as a mixture in all proportions, as well as the physiologically acceptable salts of these derivatives.

According to the invention, the C-glycoside derivatives corresponding to formula (1) preferably used as amphiphilic agents, especially as emulsifiers, as surfactants (detergents, foaming agents) or as agents capable of forming lamellar phases leading to lipid vesicles, are those defined as preferential previously in the text.

The composition according to the invention may be ingested, injected or applied to the skin (on any cutaneous zone of the body), the hair, the nails or the mucous membranes (buccal, jugal, gingival, genital, conjunctival).

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Selon le mode d'administration, la composition de l'invention peut se présenter sous toutes les formes galéniques normalement utilisées, particulièrement en cosmétologie.

Depending on the mode of administration, the composition of the invention may be in any galenical form normally used, particularly in cosmetology.

A preferred composition of the invention is a cosmetic composition intended for topical application.

The composition according to the invention contains a physiologically acceptable medium, that is to say compatible with the skin, the lips, the scalp, the eyes and / or the hair.

For topical application to the skin, the composition according to the invention may have the form in particular of an aqueous or oily solution or of the lotion or serum-type dispersion, of emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersion. a fatty phase in an aqueous phase (O / W) or conversely (W / O), or suspensions or emulsions of soft consistency of the cream or gel type aqueous or anhydrous, or microcapsules or microparticles, or vesicular dispersions ionic and / or nonionic type.

These compositions are prepared according to the usual methods.

The composition according to the invention obviously comprises a cosmetically acceptable carrier and may be in any of the galenical forms normally used for topical application, in particular in the form of an aqueous, hydroalcoholic or oily solution, an oil-in-water emulsion or water-in-oil or multiple, an aqueous or oily gel, a liquid anhydrous product, pasty or solid, an oil dispersion in an aqueous phase using spherules, these spherules may be polymeric nanoparticles such as nanospheres and nanocapsules or better lipid vesicles of ionic and / or nonionic type.

This composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse . It can optionally be applied to the skin in the form of an aerosol. It can also be in solid form, and by

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exemple sous forme de stick. Elle peut être utilisée comme produit de soin, comme produit de nettoyage, comme produit de maquillage ou encore comme simple produit déodorant.

example in the form of a stick. It can be used as a care product, as a cleaning product, as a makeup product or as a simple deodorant product.

The composition according to the invention may also be a composition for hair care, and in particular a shampoo, a setting lotion, a treatment lotion, a cream or a styling gel, a dye composition (especially oxidation dyes) in the form of coloring shampoos, restructuring lotions for the hair, a permanent composition (in particular a composition for the first time of a perm), a lotion or an anti-fall gel, a pest control shampoo, etc.

The amounts of the various constituents of the compositions that can be used according to the invention are those conventionally used in the fields under consideration.

These compositions comprise creams for cleaning, protection, treatment or care for the face, for the hands, for the feet, for large anatomical folds or for the body, (for example, day creams, night creams, make-up removing creams, foundation creams, sunscreen creams), fluid foundations, make-up removing milks, protective or skincare body milks, after-sun milks, lotions, gels or mousses for the care of the skin. skin, such as cleaning lotions, sunscreen lotions, artificial tanning lotions, bath compositions, deodorant compositions comprising a bactericidal agent, post-treatment gels or lotions, depilatory creams, anti-puncture compositions, insects, anti-pain compositions, compositions for treating certain skin diseases such as eczema, rosacea, psoriasis, lichens, severe pruritus.

The compositions according to the invention may also consist of solid preparations constituting soaps or cleaning bars.

The compositions according to the invention can also be packaged in the form

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d'une composition pour aérosol comprenant également un agent propulseur sous pression.

an aerosol composition also comprising a propellant under pressure.

In a known manner, the composition of the invention may also contain the usual adjuvants in the cosmetic and dermatological fields, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, perfumes, fillers (kaolin), filters, pigments, chelating agents, odor absorbers, dyestuffs, basic agents (triethanolamine, sodium hydroxide) or acids and further lipid vesicles. The amounts of these various adjuvants are those conventionally used in the fields under consideration, and for example from 0.01% to 30% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase, into the aqueous phase, into the lipid vesicles and / or into the nanoparticles.

In the case where C-glycoside derivatives corresponding to formula (1) are used as amphiphilic agents these adjuvants and their concentrations must be such that they do not modify the desired property for the composition according to the invention.

As oils or waxes that may be used in the invention, mention may be made of mineral oils (liquid petroleum jelly), vegetable oils (liquid fraction of shea butter, sunflower oil), synthetic oils (Purcellin oil), oils or silicone waxes (cyclomethicone) and fluorinated oils (perfluoropolyethers), bees, carnauba or paraffin waxes. To these oils can be added fatty alcohols and fatty acids (stearic acid); The compositions according to the invention may also comprise other emulsifiers or coemulsifiers, among which mention may be made, for example, of glycerol stearate, polysorbate 60 and the mixture of PEG-6 / PEG-32 / glycol stearate sold under the name of Tefoseo. 63 by Gattefosse, fatty acid and polyethylene glycol esters such as PEG-40 stearate, PEG-100 stearate, polyol fatty acid esters such as glyceryl stearate and tristearate of sorbitan.

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Comme solvants, on peut citer par exemple les mono-alcools linéaires ou ramifiés ayant de 1 à 8 atomes de carbone comme l'éthanol, le propanol, le butanol, l'isopropanol, l'isobutanol ; les polyéthylène glycols ayant de 6 à 80 oxydes d'éthylène ; les polyols comme le propylène glycol, l'isoprène glycol et le butylène glycol.

As solvents, mention may be made, for example, of linear or branched monoalcohols having from 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol or isobutanol; polyethylene glycols having from 6 to 80 ethylene oxides; polyols such as propylene glycol, isoprene glycol and butylene glycol.

As hydrophilic gelling agents that may be used in the invention, mention may be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids such as aluminum stearates and hydrophobic silica, ethylcellulose and polyethylene.

As hydrophilic active agents, it is possible to use proteins or protein hydrolysas, amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.

As lipophilic active agents, it is possible to use retinol (vitamin A) and its derivatives, tocopherol (vitamin E) and its derivatives, essential fatty acids, ceramides, essential oils, salicylic acid and its derivatives.

Preferably, the present invention relates to a composition in the form of an O / W or W / O emulsion characterized in that it comprises at least one C-glycoside derivative of formula (1).

Advantageously, the C-glycoside derivatives of formula (1) according to the invention make it possible, in particular, to produce surfactant-free emulsions conventionally used and thus have the advantage of not being irritating for particularly sensitive skin.

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Ainsi qu'indiqué ci-dessus, les compositions selon l'invention peuvent être plus ou moins fluides et elles peuvent donc se présenter sous forme de sérum, de lait, de crème ou de pâte. Ces compositions sont préparées selon les méthodes usuelles.

As indicated above, the compositions according to the invention may be more or less fluid and may therefore be in the form of serum, milk, cream or paste. These compositions are prepared according to the usual methods.

The compositions, objects of the invention, find their application in particular in a large number of cosmetic treatments of the skin, lips and hair, including the scalp, in particular for the treatment, protection, care, removal of makeup and / or cleaning the skin, lips and / or hair, and / or for makeup of the skin and / or lips. They can also be used for the treatment of dry skin and / or dry lips.

The compositions according to the invention may, for example, be used as skincare, make-up removal and / or facial cleansing products in the form of creams or milks or as makeup products (skin and lips) by incorporation of fillers or dyes. .

Other characteristics and advantages of the invention will emerge more clearly from the examples which follow, given by way of illustration and not limitation. In what follows or what precedes, the proportions are given in percentage by weight, unless otherwise indicated.

Example 1 Synthesis of a C-glycoside derivative corresponding to formula (1) with X corresponding to -CO-Synthesis of 1-deoxy, 1- (2'-oxo) heptyt-p-D-glucose.

Reaction scheme

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Mode Opératoire : Dans un tricol de 25 ml muni d'un réfrigérant, d'un thermomètre ainsi que d'une agitation magnétique, on dissout le D-glucose (500 mg, 2,8 mmol) dans 4 ml d'eau et 2 ml d'éthanol puis on additionne la 2,4-nonanedione (1,2 équivalent, 520 mg) et le bicarbonate de sodium (1,5 équivalent, 350 mmol). Le mélange est agité pendant 6 heures à 100oC. Le milieu réactionnel est ensuite lavé avec du dichlorométhane (2 fois 10 ml). La phase aqueuse est passée sur une résine Dowex SOX-200 qui a été préalablement conditionnée par des lavages aqueux (la solution finale est à pH 3-4). On concentre puis on co-évapore avec de l'isopropanol.

Procedure: In a 25 ml three-neck flask equipped with a condenser, a thermometer and a magnetic stirrer, the D-glucose (500 mg, 2.8 mmol) is dissolved in 4 ml of water and 2 ml of ethanol and then added 2,4-nonanedione (1.2 equivalents, 520 mg) and sodium bicarbonate (1.5 equivalents, 350 mmol). The mixture is stirred for 6 hours at 100oC. The reaction medium is then washed with dichloromethane (2 times 10 ml). The aqueous phase is passed over a Dowex SOX-200 resin which has been previously conditioned by aqueous washes (the final solution is at pH 3-4). Concentrate and then co-evaporate with isopropanol.

The light brown oil obtained is dried under vacuum (a yield of 76%).

 RMN'H: in accordance with the expected structure.

Example 2 for a shampoo base: sodium lauryl ether sulfate 47.5% (2. 2 mol EO) with 26% of active matter Sodium cocoamphodiacetate 6.6% (at 38% active ingredient) JR 400 (AMERCHOL) 0, 5% Derived from Example 1 3.0% Ph QSP Adjuster 6.5% Water qs 100.0%

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Exemple 3 : shampooing contenant une silicone : Lauryl ether sulfate de sodium 47, 5% Sodium cocoamphocarboxyglycinate 8, 0 % (MIRANOL C2M de RHODIA) Polydimethylsiloxane de visc. 500 000 2, 7% JR 400 d'AMERCHOL 0, 5% Monoisopropanolamide 2, 0% 1- (Hexadécyloxy)-2-octadécanol/2. 5% alcool cétylique Dérivé de l'exemple 1 4 % Conservateur qsp Ajusteur de ph qsp Ph 7 Eau qsp 100 Exemple 4 : Emulsion type après shampooing : Mélange alcool cetylstéarylique/4% alcool cetylstéarylique oxyethyléné (300E) Chlorure de béhényltrimethylammonium 2% à 80% dans un mélange eau/isopropanol15/85 GENAMIN KDMP de CARIANT Dérivé de l'exemple 1 4 % conservateur qsp Ajustement de Ph 4-5 Eau QSP 100 Exemple 5 gel douche corporel lauryl ether sulfate de sodium 7% Dérivé de l'exemple 1 5% polyquaternium 7 0.2% Merquat S de Calgon PEG 120 methyl glucose dioléate 2% Glucamate DOE120 Végétât de Amerchol

EXAMPLE 3 Shampoo containing a Silicone: Sodium Lauryl Ether Sulfate 47.5% Sodium Cocoamphocarboxyglycinate 8.0% (MIRANOL C2M from Rhodia) Polydimethylsiloxane from visc. 500,000 2.7% JR 400 AMERCHOL 0.5% Monoisopropanolamide 2.0% 1- (Hexadecyloxy) -2-octadecanol / 2. 5% cetyl alcohol Derivative of Example 1 4% Preservative qsp Ph adjustor qsp Ph 7 Water qs 100 Example 4: Emulsion type after shampoo: Cetylstearyl alcohol mixture / 4% cetylstearyl alcohol oxyethylenated (300E) Behenyltrimethylammonium chloride 2% to 80 % in a mixture of water / isopropanol15 / 85 GENAMIN KDMP of CARIANT Derivative of Example 1 4% preservative qs Adjustment of Ph 4-5 Water QSP 100 Example 5 body shower gel lauryl ether sodium sulfate 7% Derived from Example 1 5% polyquaternium 7 0.2% Merquat S from Calgon PEG 120 methyl glucose dioleate 2% Glucamate DOE120 Amerchol Vegetate

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conservateur 0. 3% disodium EDTA 0. 1% eau qsp 100% Exemple 5 : gel nettoyant moussant visage peau à tendance grasse lauryl phosphate 6.5% MAP20 de Kao Chemicals Dérivé de l'exemple 1 6.5% PEG 150 pentaerythrityl tetrastearate 0.5% CROTHIX de Croda KOH 1.7% conservateur 0.3%

disodium EDTA 0. 1% eau qsp 100%

preservative 0. 3% disodium EDTA 0. 1% water qs 100% EXAMPLE 5 Kao Chemicals 6.5% MAP20 Moisturizing Face Skin Lotion-Lauryl Phosphate Cleansing Gel Derived from Example 1 6.5% PEG 150 pentaerythrityl tetrastearate 0.5% CROTHIX Croda KOH 1.7% preservative 0.3%

disodium EDTA 0. 1% water qs 100%

Claims (25)

 1. C-glycoside derivatives having the formula (1):

 in which - S represents a monosaccharide or a polysaccharide up to 20 sugar units, in pyranose and / or furanose form and of series L and / or D, said mono- or polysaccharide having at least one hydroxyl function which is necessarily free and optionally or more amine function possibly protected; - at ! S-CHz-X is a C-anomeric bond; X represents a group chosen from: -CO-, -CH (OH) -, -CH (NRiR2) -, -CHR '-, - C (= CHR') -; R represents a linear or branched alkyl, arylalkyl, perfluoroalkyl, hydrofluoroalkyl, saturated or unsaturated chain, a cycloalkyl, cycloperfluoroalkyl, cyclohydrofluoroalkyl or aryl ring, comprising from 5 to 28 carbon atoms, the said chain and / or said ring possibly being interrupted; with one or more heteroatoms chosen from oxygen, sulfur, nitrogen, silicon, and optionally substituted with at least one radical chosen from -OR'1, -SR "1, -NR '' '1R'2, -COO '' 2, -CONHR '' '2, - CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical; R' is hydrogen, alkyl, arylalkyl, perfluoroalkyl, linear or branched, saturated or unsaturated hydrofluoroalkyl, a cycloalkyl, cycloperfluoroalkyl, cyclohydrofluoroalkyl, aryl ring, comprising 1 to 28 carbon atoms, said chain or said cycle being <Desc / Clms Page number 30>  optionally interrupted by one or more heteroatoms chosen from oxygen, sulfur, nitrogen, silicon, and optionally substituted with at least one radical chosen from -OR'1, -SR "1, -NR''1R'2 , -COOR "2, -CONHR" '2, - CN, halogen, perfluoroalkyl, hydrofluoroalkyl or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical; R 1, R 2, R' 1, R '2, R "R 2, R''1, R "'2, identical or different, represent a hydrogen atom, a hydroxyl, a radical chosen from a linear or branched, saturated or unsaturated, perfluoroalkyl and / or hydrofluoroalkyl radical, comprising from 1 to at 30 carbon atoms.

2. C-glycoside derivatives corresponding to the formula (1) as defined in the claim, characterized in that S represents a monosaccharide or a polysaccharide containing up to 6 sugar units, in the pyranose and / or furanose and L-series form and / or D, said mono-or polysaccharide having at least one hydroxyl function necessarily free and / or optionally one or more optionally protected amine function. 3. C-glycoside derivatives corresponding to formula (1) as defined in any one of the preceding claims, characterized in that S represents a monosaccharide selected from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, N-acetyl-D-glucosamine, L-fucose, L-arabinose, Lrhamnose, 4. C-glycoside derivatives corresponding to formula (1) as defined in any one of the preceding claims, characterized in that S represents a monosaccharide selected from D-glucose, D-xylose, N-acetyl- D-glucosamine, L-fucose.

5. C-glycoside derivatives corresponding to formula (1) as defined in any one of the preceding claims, characterized in that S represents D-glucose. <Desc / Clms Page number 31>

 6. C-glycoside derivatives corresponding to formula (1) as defined in any one of claims 1 and 2, characterized in that S represents a polysaccharide containing up to 6 sugar units. 7. C-glycoside derivatives corresponding to formula (1) as defined in any one of claims 1, 2 and 6, characterized in that S represents a polysaccharide containing up to 6 sugar units chosen from D-maltotriose , D-maltose, D-lactose, D-cellobiose. 8. C-glycoside derivatives corresponding to formula (1) as defined in any one of claims 1, 2, 6 and 7, characterized in that S represents a polysaccharide containing up to 6 sugar units chosen from D -maltose, D-lactose, D-cellobiose. 9. C-glycoside derivatives corresponding to formula (1) as defined in any one of the preceding claims, characterized in that X represents a group chosen from -CO-, -CH (OH) -, - CH (NRiR2 ) -, - CHz -, - C (= CHR ') - with R, R', R1, R2, R'1, R'2, R "1, R" 2, R "'1, R"' 2 as defined in claim 1. 10. C-glycoside derivatives corresponding to formula (1) as defined in any one of the preceding claims, characterized in that X represents a group chosen from -CO- or -CH (OH) -, with R, R R 1, R "2, R" 1, R "2, R" 'R' '2 as defined in claim 1. 11. C-glycoside derivatives having the formula (1) as defined in one

 any of the preceding claims, selected from: - 1-deoxy, 1- (2'-oxo) heptyt-p-D-ce) tobiose; - 1-deoxy, 1- (2'-oxo) heptyl-α-D-c-onobiosis; 1-deoxy, 1- (2'-oxo) octyl-p-D-cellobiose; 1-deoxy, 1- (2'-oxo) octyl-α-D-cobibose; 1-deoxy, 1- (2'-oxo) decyl-p-D-cellobiose; - 1-deoxy, 1- (2'-oxo) decyt-α-D-cettobiose; <Desc / Clms Page number 32>  1-deoxy, 1- (2'-oxo) tetradecyl-ss-D-cellobiose; - 1-deoxy, 1- (2'-oxo) tetradecyl! -A-D-ce! ! obiose; 1-deoxy, 1- (2'-oxo) hexadecyl-ss-D-cellobiose; 1-deoxy, 1- (2'-oxo) hexadecyl) -α-D-cet) obiosis; 1-deoxy, 1- (2'-oxo) octadecyl-p-D-cellobiose; 1-deoxy, 1- (2'-oxo) octadecyl-α-D-cellobiose-1-deoxy, 1- (2'-oxo) nonadecyl-p-D-cellobiose; 1-deoxy, 1- (2'-oxo) n-onadecyl-α-D-celobutyne-1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-p-D-cellobiose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-cellobiose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-p-D-cellobiose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-cellobiose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Dcellobiose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dcellobiose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-cellobiose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD -cellobiose; 1-deoxy, 1- (2'-oxo-2'-undecaf) uorocyclohexyl) ethyl-P-D-ceftobiose; - 1-deoxy, 1- (2'-oxo-2'-undecaf) uorocyctohexy) ethyl-α-D-α-1α) obiosis; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-ss-D-cellobose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyf-a-D-3-yl) obiosis; 1-deoxy, 1- (2'-oxo-2'-phenyl) -o-hydroxyphenyl) ethyl) -P-D-cetiobiosis; 1-deoxy, 1- (2'-oxo-2'-phenyl) -o-hydroxyphenyl) ethyl-α-D-cetiobiosis; - 1-deoxy, 1- (2'-amino) heptyl-p-D-ce! tobiose; - 1-deoxy, 1- (2'-amino) heptyl-α-D-this obiose; 1-deoxy, 1- (2'-hydroxyoxy) heptyl-p-D-celobutyne-1-deoxy, 1- (2'-hydroxy) heptyl-α-D-tl) tobiosis; 1-deoxy, 1- (2'-oxo) heptyl-p-D-glucose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-glucose;

<Desc / Clms Page number 33>  1-deoxy, 1- (2'-oxo) octyl-p-D-glucose; - 1-deoxy, 1- (2'-oxo) octy! -A-D-g! ucose; 1-deoxy, 1- (2'-oxo) decyl) -p-D-g! ucose; 1-deoxy, 1- (2'-oxo) decyl-α-D-g) ucose; 1-deoxy, 1- (2'-oxo) tetradecyl-p-D-glucose; 1-deoxy, 1- (2'-oxo) tetradecyl) -α-D-glucose; 1-deoxy, 1- (2'-oxo) hexadecyl-p-D-glucose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-glucose; 1-deoxy, 1- (2'-oxo) octadecyl, -P-D-glucose; 1-deoxy, 1- (2'-oxo) octadecyl-α-D-glucose-1-deoxy, 1- (2'-oxo) nonadecyl-β-D-glucose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-glucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-p-D-g! ucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-glucoside; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-p-D-glucose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl) -α-D-g! ucose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Dglucose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dglucose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-glucose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD -glucose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-p-D-glucose; 1-deoxy, 1- (2'-oxo-2'-undecaf) uorocyclohexyl) ethyl) -α-D-glucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-p-D-glucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl) -α-D-g) ucose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-β-D-g! ucose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-α-D-glucose; 1-deoxy, 1- (2'-amino) heptyl-p-D-glucose; 1-deoxy, 1- (2'-amino) heptyl-α-D-glucose;

<Desc / Clms Page number 34>  - 1-deoxy, 1- (2'-hydroxy) heptyl-p-D-glucose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-glucose; 1-deoxy, 1- (2'-oxo) heptyl-p-D-maltose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-mattose; 1-deoxy, 1- (2'-oxo) octyl-p-D-maltose; 1-deoxy, 1- (2'-oxo) octyl-α-D-maltose; 1-deoxy, 1- (2'-oxo) decyl-p-D-maltose; 1-deoxy, 1- (2'-oxo) decyl-α-D-maltose; 1-deoxy, 1- (2'-oxo) tetradecyl-β-D-ma! tose; 1-deoxy, 1- (2'-oxo) tetradecyl-α-D-methyl; 1-deoxy, 1- (2'-oxo) hexadecyl-p-D-maltose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-mattose; 1-deoxy, 1- (2'-oxo) octadecyl) -3-D-ma) tose; 1-deoxy, 1- (2'-oxo) octadecyl-α-D-maltose; 1-deoxy, 1- (2'-oxo) nonadecyl-p-D-maltose; 1-deoxy, 1- (2'-oxo) nonadecyl) -α-D-maitose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-p-D-maltose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-maltose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-s-D-maltose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-maltose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Dmaltose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dmaltose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl-ss; D-maltose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD -maltose; 1-deoxy, 1- (2'-oxo-2'-undecaftuorocyclohexy) ethyl-p-D-ma) tose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-D-maltose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl) -3-D-mattose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-D-maitose;

<Desc / Clms Page number 35>  1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-maltose-1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl -aD-ma! tose; 1-deoxy, 1- (2'-amino) heptyl-p-D-maltose; - 1-deoxy, 1- (2'-amino) heptyl-α-D-ma! tose; 1-deoxy, 1- (2'-hydroxy) heptyl-p-D-maitose-1-deoxy, 1- (2'-hydroxy) heptyl) -α-D-ma! tose; 1-deoxy, 1- (2'-oxo) heptyl-p-D-lactose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-lactose; 1-deoxy, 1- (2'-oxo) octyl-p-D-lactose; 1-deoxy, 1- (2'-oxo) octyl-α-D-tactose; 1-deoxy, 1- (2'-oxo) decyl-p-D-lactose-1-deoxy, 1- (2'-oxo) decyl-α-D-lactose; 1-deoxy, 1- (2'-oxo) tetradecyl-p-D-lactose-1-deoxy, 1- (2'-oxo) tetradecyl-α-D-lactose; 1-deoxy, 1- (2'-oxo) hexadecyl-p-D-lactose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-lactose; 1-deoxy, 1- (2'-oxo) octadecyl-p-D-lactose; 1-deoxy, 1- (2'-oxo) octadecyl-α-D-lactose; 1-deoxy, 1- (2'-oxo) nonadecyl-p-D-lactose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-lactose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-p-D-lactose-1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-lactose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-p-D-lactose-1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-lactose; 1-deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octy p-Dlactose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dlactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-lactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl); dD-lactose;

<Desc / Clms Page number 36>  1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-p-D-lactose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-D-lactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-p-D-lactose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-D-lactose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-lactose-1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl) dD-lactose; 1-deoxy, 1- (2'-amino) heptyl-p-D-lactose; 1-deoxy, 1- (2'-amino) heptyl-α-D-lactose; 1-deoxy, 1- (2'-hydroxy) heptyl-p-D-lactose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-lactose; 1-deoxy, 1- (2'-oxo) heptyl-p-N-acetyl-D-glucosamine-1-deoxy, 1- (2'-oxo) heptyl-α-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) octyl-p-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) octyl-α-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) decyl) -N-acetyl) -D-g! ucosamine; 1-deoxy, 1- (2'-oxo) decyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) tetradecyl-p-N-acetyl-D-glucosamine 1-deoxy, 1- (2'-oxo) tetradecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) hexadecyl-p-N-acetyl-D-glucosamine-1-deoxy, 1- (2'-oxo) hexadecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) octadecyl-N-acetyl-D-g) ucosamine; 1-deoxy, 1- (2'-oxo) octadecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) nonadecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo) nonadecyl-α-N-acetyl-D-g) ucosamine; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-pN-acetyl-D-glucosamine-1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-N-acetyl- D-glucosamine; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'nonaf) uoro-4 ', 7'-dioxa octyl) -) 3-Nacetyl-D-glucosamine; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl α-N-acetyl-D-glucosamine;

<Desc / Clms Page number 37>  1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl- ss-N-acetyl-D-glucosamine; 1-Deoxy, 1- (2'-oxo-3'-fluorophenyl) -3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl- N-acetyl-D-glucosamine; 9-1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-p-N-acetyl-Dglucosamin; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-N-acetyl-Dglucosamin; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-p-N-acetyl-D-g) ucosamine; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-N-acetyl-D-g) ucosamine; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-p-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-N-acetyl) -glucosamin; 1-deoxy, 1- (2'-amino) heptyl-p-N-acetyl-D-glucosamine-1-deoxy, 1- (2'-amino) heptyl-α-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-hydroxy) heptyl-p-N-acetyl-D-glucosamine; 1-deoxy, 1- (2'-hydroxy) heptyl-N-acetyl) -D-g! ucosamine; 1-deoxy, 1- (2'-oxo) heptyl-3-D-xytose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-xylose: 1-deoxy, 1- (2'-oxo) octyl-p-D-xyloseose; 1-deoxy, 1- (2'-oxo) octyl-α-D-xyl dare; 1-deoxy, 1- (2'-oxo) decyl) -3-D-xyl! dare; 1-deoxy, 1- (2'-oxo) decyl-α-D-xylase; 1-deoxy, 1- (2'-oxo) tetradecyl-pD-xylose 1-deoxy, 1- (2'-oxo) tetradecyl-α-D-xylose-1-deoxy, 1- (2'-oxo) hexadecyl p-xylose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-xyloseose; 1-deoxy, 1- (2'-oxo) octadecyl-p-D-xylose; 1-desoxy, 1- (2'-oxo) octadecyl! -Α-D-xyl! dare; 1-deoxy, 1- (2'-oxo) nonadecyl-p-D-xylose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-xytose;

<Desc / Clms Page number 38>  1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-p-D-xylose-1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-xylose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-s-D-xylose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-xylose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl p-Dxylose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dxylose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-xylose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl aD -xy! dare; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-ss-D-xylose; 1-deoxy, 1- (2'-oxo-2'-undecaftuorocyclohexyl) ethyl-α-D-xylose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-p-D-xylose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-D-xylose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-p-D-xylose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-α-D-xylose; 1-deoxy, 1- (2'-amino) heptyl-p-D-xyloseose; 1-deoxy, 1- (2'-amino) heptyl-α-D-xylose; 1-deoxy, 1- (2'-hydroxy) heptyl-p-D-xylose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-xylose; 1-deoxy, 1- (2'-oxo) heptyl-p-L-fucose; 1-deoxy, 1- (2'-oxo) heptyl-α-L-fucose; 1-deoxy, 1- (2'-oxo) octyl-p-L-fucose; 1-deoxy, 1- (2'-oxo) octyl-α-L-fucose; 1-deoxy, 1- (2'-oxo) decyl-β-L-fucose; 1-deoxy, 1- (2'-oxo) decyl-α-L-fucose; 1-deoxy, 1- (2'-oxo) tetradecyl- (3-L-fucose) -1-deoxy, 1- (2'-oxo) tetradecyl-α-fucose, 1-deoxy, 1- -oxo) hexadecyl- (3-L-fucose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-fucose;

<Desc / Clms Page number 39>  1-deoxy, 1- (2'-oxo) octadecyl-s-L-fucose; 1-deoxy, 1- (2'-oxo) octadecyl-α-L-fucose; 1-deoxy, 1- (2'-oxo) nonadecyl-P-L-fucose-1-deoxy, 1- (2'-oxo) nonadecyl-α-L-fucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-s-L-fucose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-L-fucose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-p-L-fucose-1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-L-fucose; 1-deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octy ) pfucose; 1-deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa ) octyt-a-lactose; 1-deoxy, 1- (2'-oxo-3'-thfluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-pL-fucose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro (4') oxaheptyl); aL-fucose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-p-L-fucose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-L-fucose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-p-t-fucose-1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-L-fucose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pL-fucose-1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl- aL-fucose; 1-deoxy, 1- (2'-amino) heptyl-β-L-fucose-1-deoxy, 1- (2'-amino) heptyl-α-L-fucose; 1-deoxy, 1- (2'-hydroxy) heptyl-ss-L-fucose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-L-fucose; 1-deoxy, 1- (2'-oxo) heptyl-p-D-mannose; 1-deoxy, 1- (2'-oxo) heptyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) octyl-pD-mannose 1-deoxy, 1- (2'-oxo) octyl-α-D-mannose-1-deoxy, 1- (2'-oxo) decyl-pD-mannose; 1-deoxy, 1- (2'-oxo) decyl-α-D-mannose;

<Desc / Clms Page number 40>  1-deoxy, 1- (2'-oxo) tetradecyl-p-D-mannose; 1-deoxy, 1- (2'-oxo) tetradecyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) hexadecyl- (3-D-mannose) -1-deoxy, 1- (2'-oxo) hexadecyl-α-D-mannose, 1-deoxy, 1- (2'-oxo) octadecyl-pD-mannose; 1-deoxy, 1- (2'-oxo) octadecyl) -α-mannose; 1-deoxy, 1- (2'-oxo) nonadecyl-p-D-mannose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-mannose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-s-D-mannose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-mannose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-p-D-mannose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-mannose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Dmannose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -a-Dmannose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-ss -D-mannose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD -mannose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocydohexyl) ethyl) -) 3-D-mannose; 1-deoxy, 1- (2'-oxo-2'-undecaffurorocyclohexyl) ethyl-α-D-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-p-D-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl-α-D-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-p-D-mannose; 1-deoxy, 1- (2'-oxo-2'-phenyl) -o-hydroxyphenyl) ethyl) -α-D-mannose; 1-deoxy, 1- (2'-amino) heptyl-p-D-mannose; 1-deoxy, 1- (2'-amino) heptyl-α-D-mannose; 1-deoxy, 1- (2'-hydroxy) heptyl-3-D-mannose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-mannose; 1-deoxy, 1- (2'-oxo) heptyl-p-D-galactose; - 1-deoxy, 1- (2'-oxo) heptyl) -a-D-ga! actose;

<Desc / Clms Page number 41>  1-deoxy, 1- (2'-oxo) octy! -P-D-ga! actose; - 1-deoxy, 1- (2'-oxo) octy! -A-D-ga! actose; 1-deoxy, 1- (2'-oxo) decyl-β-D-galactose; - 1-deoxy, 1- (2'-oxo) decyl-a-D-ga! actose, 1-deoxy, 1- (2'-oxo) tetradecyl-p-D-lactose-1-deoxy, 1- (2'-oxo) tetradecyl-a-D-ga! actose; - 1-deoxy, 1- (2'-oxo) hexadecyl) -) 3-D-ga! actose; 1-deoxy, 1- (2'-oxo) hexadecyl-α-D-galactose; 1-deoxy, 1- (2'-oxo) octadecyl-p-D-lactose-1-deoxy, 1- (2'-oxo) octadecyl-a-D-ga! actose; 1-deoxy, 1- (2'-oxo) nonadecyl-β-D-galactose; 1-deoxy, 1- (2'-oxo) nonadecyl-α-D-gatactose; 1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-β-D-galactose-1-deoxy, 1- (2'-oxo-10'-ene) nonadecyl-α-D-galactose; 1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-β-D-galactose-1-deoxy, 1- (2'-oxo-10,13-diene) nonadecyl-α-D-galactose; 1-Deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa) octyl -ss-Dgalactose; 1-deoxy, 1- (2'-oxo-3 ', 3', 5 ', 5', 6 ', 6', 8 ', 8', 8'-nonafluoro-4 ', 7'-dioxa ) octyi-a-Dgalactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5, 6 ', 6', 7 ', 7', 7'-octafluoro-4 ') oxaheptyl-s-D -galactose; 1-Deoxy, 1- (2'-oxo-3'-trifluoromethyl-3 ', 5', 5 ', 6', 6 ', 7', 7 ', 7'-octafluoro-4') oxaheptyl-aD -galactose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-p-D-galactose; 1-deoxy, 1- (2'-oxo-2'-undecafluorocyclohexyl) ethyl-α-D-galactose; 1-desoxy, 1- (2'-oxo-2'-phenyl) ethyl- (3-D-ga! Actose; 1-deoxy, 1- (2'-oxo-2'-phenyl) ethyl); α-DHA-actose, 1-deoxy, 1- (2'-oxo-2'-phenyl-o-hydroxyphenyl) ethyl-pD-galactose, 1-deoxy, 1- (2'-oxo-2 ') phenyl) -o-hydroxyphenyl) ethyl) -α-D-ga) actose; 1-deoxy, 1- (2'-amino) heptyl) - (3-D-ga) actose; 1-deoxy, 1- (2'-amino) heptyl-α-D-ga) actose;

<Desc / Clms Page number 42>  1-deoxy, 1- (2'-hydroxy) heptyl-3-D-gatactose; 1-deoxy, 1- (2'-hydroxy) heptyl-α-D-galactose.

12. Process for the preparation of the new C-glycoside derivatives corresponding to formula (1) as defined in any one of the preceding claims, for which X corresponds to -CO-, characterized in that it consists of: - dissolving in water or in a mixture of water and a water-miscible solvent, 1 equivalent of a monosaccharide or a polysaccharide of the formula S as defined in any preceding claim, to be added between 1 and 5 equivalents of a ss-diketone compound of the general formula R "-CO-CH 2 -CO-R, with R and R" as defined in claim 1 it being understood that R "is different from hydrogen, and between 1 and 5 equivalents of an organic or mineral base, and heating the reaction mixture to a temperature between 40 and 110 cl, for a period of between 3 and 30h, and then, after cooling, washing the reaction medium with an organic solvent which can be chosen in particular from ethyl acetate,

 dichloromethane, diethyl ether, disopropyl ether, terbutyl methyl ether, methyl ethyl ketone, - to neutralize the aqueous phase with a mineral or organic acid or by passing over an acidic resin, - to concentrate and then to co-evaporate with an organic solvent chosen from: ethanol, methanol, toluene and / or isopropanol, - to dry under vacuum the product obtained, then optionally to purify by chromatography and / or crystallization. 13. Preparation process according to the preceding claim, characterized in that the polar protic solvent is selected from tetrahydrofuran, dioxane, N-methyl-pyrrolidone, glycerol, dimethylsulfoxide, acetate

 ethyl, tert-butyl-methyl-ether, pyridine, isopropanol, dimethylformamide, acetonitrile, dichloromethane, and alcohols. <Desc / Clms Page number 43>

 14. Preparation process according to any one of claims 12 and 13, characterized in that the polar protic solvent is ethanol. 15. Preparation process according to any one of claims 12 to 14, characterized in that the base is a mineral base. 16. Preparation process according to any one of claims 12 to 15, characterized in that the reaction mixture is heated to a temperature between 75 and 100 OC. 17. Preparation process according to any one of claims 12 to 16, characterized in that the heating time is between 5 and 18h. 18. Composition comprising at least one C-glycoside derivative of formula (1) as defined according to any one of claims 1 to 11. 19. Composition according to the preceding claim characterized in that it is intended for a cosmetic or pharmaceutical use, 20. Composition according to any one of claims 18 and 19 characterized in that it comprises at least one C-glycoside derivative corresponding to formula (1) in an amount representing from 0.1% to 50% of the total weight of the composition. 21. Composition according to any one of claims 18 to 20 characterized in that it comprises at least one C-glycoside derivative corresponding to formula (1) in an amount representing from 0.5% to 20% of the total weight of the composition. 22. Use of at least one C-glycoside derivative corresponding to formula (1), as defined according to any one of claims 1 to 11, as amphiphilic agent. <Desc / Clms Page number 44>

23. Use of at least one C-glycoside derivative corresponding to formula (1), as defined according to any one of claims 1 to 11, as emulsifying agent. 24. Use of at least one C-glycoside derivative corresponding to formula (1), as defined according to any one of claims 1 to 11, as surfactants. 25. Use of at least one C-glycoside derivative corresponding to formula (1), as defined according to any one of claims 1 to 11, as agents capable of forming lamellar phases leading to lipid vesicles.