FI71159C - 4'-halogensubstituerade sackarosderivat - Google Patents

4'-halogensubstituerade sackarosderivat Download PDF

Info

Publication number: FI71159C
Authority: FI; Finland
Prior art keywords: atom; denote; ether; halogen; halogen atom
Prior art date: 1981-08-21

Application number

FI821486A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI821486A0 (fi

FI71159B (fi

FI821486L (fi

Inventor

Graham Jackson

Michael Ralph Jenner

Riaz Ahmed Khan

Cheang Kuan Lee

Khizar Sultan Mufti

Gita Dilip Patel

Elner Brean Rathbone

Original Assignee

Tate & Lyle Plc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-08-21

Filing date

1982-04-28

Publication date

1986-11-24

1982-04-28 Application filed by Tate & Lyle Plc filed Critical Tate & Lyle Plc

1982-04-28 Publication of FI821486A0 publication Critical patent/FI821486A0/fi

1983-02-22 Publication of FI821486L publication Critical patent/FI821486L/fi

1986-08-14 Application granted granted Critical

1986-08-14 Publication of FI71159B publication Critical patent/FI71159B/fi

1986-11-24 Publication of FI71159C publication Critical patent/FI71159C/fi

Links

229910052736 halogen Inorganic materials 0.000 title claims description 11
150000001875 compounds Chemical class 0.000 claims abstract description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 37
125000005843 halogen group Chemical group 0.000 claims abstract description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 14
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 191
239000000203 mixture Substances 0.000 claims description 54
150000002118 epoxides Chemical class 0.000 claims description 18
235000003599 food sweetener Nutrition 0.000 claims description 16
-1 halogen ion Chemical class 0.000 claims description 16
239000003765 sweetening agent Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
108090000623 proteins and genes Proteins 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000005604 azodicarboxylate group Chemical group 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000004469 siloxy group Chemical class [SiH3]O* 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
239000000047 product Substances 0.000 description 93
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 79
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 63
239000011541 reaction mixture Substances 0.000 description 62
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
239000003208 petroleum Substances 0.000 description 44
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 42
229930006000 Sucrose Natural products 0.000 description 40
239000005720 sucrose Substances 0.000 description 40
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 39
239000006188 syrup Substances 0.000 description 38
235000020357 syrup Nutrition 0.000 description 38
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 32
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
230000006196 deacetylation Effects 0.000 description 16
238000003381 deacetylation reaction Methods 0.000 description 16
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
238000005660 chlorination reaction Methods 0.000 description 14
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
229920005989 resin Polymers 0.000 description 13
239000011347 resin Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 11
AHLIHMGXFJRKSY-ZQNATQRZSA-N [(2r,3r,4s,5r,6r)-4,5-diacetyloxy-6-[(2s,3s,4r,5r)-3,4-diacetyloxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](O)[C@@H](COC(=O)C)O[C@@H]1O[C@@]1(CO)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](CO)O1 AHLIHMGXFJRKSY-ZQNATQRZSA-N 0.000 description 11
150000003445 sucroses Chemical class 0.000 description 11
239000005457 ice water Substances 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 9
235000009508 confectionery Nutrition 0.000 description 9
230000003197 catalytic effect Effects 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
238000006884 silylation reaction Methods 0.000 description 8
239000011734 sodium Substances 0.000 description 8
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 8
230000021736 acetylation Effects 0.000 description 7
238000006640 acetylation reaction Methods 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
150000002367 halogens Chemical group 0.000 description 7
239000007858 starting material Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000005828 desilylation reaction Methods 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 6
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
206010013911 Dysgeusia Diseases 0.000 description 4
102000011782 Keratins Human genes 0.000 description 4
108010076876 Keratins Proteins 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
235000013361 beverage Nutrition 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
229920001429 chelating resin Polymers 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
239000003826 tablet Substances 0.000 description 4
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 4
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
230000031709 bromination Effects 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229940112822 chewing gum Drugs 0.000 description 3
235000015218 chewing gum Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 3
229940034610 toothpaste Drugs 0.000 description 3
239000000606 toothpaste Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
229920002774 Maltodextrin Polymers 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013058 crude material Substances 0.000 description 2
229940109275 cyclamate Drugs 0.000 description 2
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000019520 non-alcoholic beverage Nutrition 0.000 description 2
239000001814 pectin Substances 0.000 description 2
235000010987 pectin Nutrition 0.000 description 2
229920001277 pectin Polymers 0.000 description 2
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 2
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
238000010791 quenching Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
UQXZSKHOYOHVIH-UGDNZRGBSA-N (2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 UQXZSKHOYOHVIH-UGDNZRGBSA-N 0.000 description 1
XXBNLUKLCXTTPH-MGCNEYSASA-N (2r,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanoyl chloride Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(Cl)=O XXBNLUKLCXTTPH-MGCNEYSASA-N 0.000 description 1
IJPVCOQVFLNLAP-MGCNEYSASA-N (2r,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanoyl fluoride Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(F)=O IJPVCOQVFLNLAP-MGCNEYSASA-N 0.000 description 1
HMZWMEWFANSYTB-AZQCALEQSA-N (3S,4S,5S)-6,6-dichloro-1-fluoro-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound ClC([C@H]([C@H]([C@@H](C(C(O)F)=O)O)O)O)(O)Cl HMZWMEWFANSYTB-AZQCALEQSA-N 0.000 description 1
JBIQXKYIGHDIID-UYFOZJQFSA-N (3r,4r,5r)-4-chloro-1,3,5,6-tetrahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](Cl)[C@H](O)C(=O)CO JBIQXKYIGHDIID-UYFOZJQFSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
VXZBYIWNGKSFOJ-UHFFFAOYSA-N 2-[4-[5-(2,3-dihydro-1H-inden-2-ylamino)pyrazin-2-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC=1N=CC(=NC=1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 VXZBYIWNGKSFOJ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
108010011485 Aspartame Proteins 0.000 description 1
GOJCZVPJCKEBQV-UHFFFAOYSA-N Butyl phthalyl butylglycolate Chemical compound CCCCOC(=O)COC(=O)C1=CC=CC=C1C(=O)OCCCC GOJCZVPJCKEBQV-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000005913 Maltodextrin Substances 0.000 description 1
101710084933 Miraculin Proteins 0.000 description 1
108050004114 Monellin Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
229910018540 Si C Inorganic materials 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
229920001938 Vegetable gum Polymers 0.000 description 1
UMOFHQSJMUINFR-UHFFFAOYSA-N [4,5-diacetyloxy-6-[3,4-diacetyloxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-2-(hydroxymethyl)oxan-3-yl] acetate Chemical compound CC(=O)OC1C(OC(=O)C)C(CO)OC1(CO)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(CO)O1 UMOFHQSJMUINFR-UHFFFAOYSA-N 0.000 description 1
230000000397 acetylating effect Effects 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000000605 aspartame Substances 0.000 description 1
235000010357 aspartame Nutrition 0.000 description 1
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
229960003438 aspartame Drugs 0.000 description 1
239000000305 astragalus gummifer gum Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
208000002925 dental caries Diseases 0.000 description 1
238000006642 detritylation reaction Methods 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000007919 dispersible tablet Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
230000003780 keratinization Effects 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000015122 lemonade Nutrition 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
229940035034 maltodextrin Drugs 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
MKZIFKDPZMAKOK-UHFFFAOYSA-N methanimidoyl chloride;hydrochloride Chemical compound [Cl-].ClC=[NH2+] MKZIFKDPZMAKOK-UHFFFAOYSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
239000004200 microcrystalline wax Substances 0.000 description 1
235000019808 microcrystalline wax Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
229940051866 mouthwash Drugs 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012088 reference solution Substances 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000012085 test solution Substances 0.000 description 1
239000000892 thaumatin Substances 0.000 description 1
235000010436 thaumatin Nutrition 0.000 description 1
229940035339 tri-chlor Drugs 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/37—Halogenated sugars

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Nutrition Science (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Seasonings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Steroid Compounds (AREA)
Outer Garments And Coats (AREA)
Cephalosporin Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI821486A 1981-08-21 1982-04-28 4'-halogensubstituerade sackarosderivat FI71159C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8125622		1981-08-21
GB8125622		1981-08-21

Publications (4)

Publication Number	Publication Date
FI821486A0 FI821486A0 (fi)	1982-04-28
FI821486L FI821486L (fi)	1983-02-22
FI71159B FI71159B (fi)	1986-08-14
FI71159C true FI71159C (fi)	1986-11-24

Family

ID=10524107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI821486A FI71159C (fi)	1981-08-21	1982-04-28	4'-halogensubstituerade sackarosderivat

Country Status (22)

Country	Link
EP (1)	EP0073093B1 (da)
JP (1)	JPS5835196A (da)
KR (1)	KR870001900B1 (da)
AT (1)	ATE10003T1 (da)
AU (1)	AU557186B2 (da)
CA (1)	CA1189070A (da)
DE (1)	DE3261037D1 (da)
DK (1)	DK158472C (da)
ES (1)	ES511753A0 (da)
FI (1)	FI71159C (da)
GB (1)	GB2104063B (da)
GR (1)	GR75418B (da)
IE (1)	IE52795B1 (da)
IL (1)	IL65621A (da)
MX (1)	MX7260E (da)
NO (1)	NO152875C (da)
NZ (1)	NZ200418A (da)
PT (1)	PT74796B (da)
SU (1)	SU1301316A3 (da)
TR (1)	TR21241A (da)
YU (1)	YU90682A (da)
ZA (1)	ZA822854B (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8403611D0 (en) *	1984-02-10	1984-03-14	Tate & Lyle Plc	Sweetener
DE3432565A1 (de) *	1984-09-05	1986-03-13	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von glycosylfluoriden
GB8818430D0 (en) *	1988-08-03	1988-09-07	Tate & Lyle Plc	Process
GB8822673D0 (en) *	1988-09-27	1988-11-02	Tate & Lyle Plc	Selective acylation of sugars
GB8822674D0 (en) *	1988-09-27	1988-11-02	Tate & Lyle Plc	Preparation of acylated sucrose derivatives
US5272146A (en) *	1992-10-02	1993-12-21	The United States Of America As Represented By The United States Department Of Health And Human Services	1,2-dihydroellipticines with activity against CNS specific cancer cell lines
US8758814B2 (en)	2004-10-08	2014-06-24	Mcneil-Ppc, Inc.	Chewable enteric coated aspirin tablets
US8057820B2 (en)	2004-10-08	2011-11-15	Mcneil-Ppc, Inc.	Enteric coated aspirin granules comingled with binder
WO2006088017A1 (ja) *	2005-02-16	2006-08-24	National University Corporation Hokkaido University	４位ハロゲン化ガラクトース含有糖鎖及びその応用
WO2018237136A1 (en) *	2017-06-21	2018-12-27	H. Lee Moffitt Cancer Center And Research Institute, Inc.	CONJUGATES FOR DETECTING AXILLARY LYMPHATIC GANGLION METASTASES

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7612668A (nl) *	1976-01-06	1977-07-08	Dow Chemical Co	Werkwijze voor het bereiden van nieuwe organo- fosforusverbindingen.
CA1183133A (en) *	1980-10-28	1985-02-26	Tate & Lyle Public Limited Company	Sweet chlorine-substituted disaccharides

1982
- 1982-04-21 DE DE8282302047T patent/DE3261037D1/de not_active Expired
- 1982-04-21 AT AT82302047T patent/ATE10003T1/de not_active IP Right Cessation
- 1982-04-21 EP EP82302047A patent/EP0073093B1/en not_active Expired
- 1982-04-21 GB GB08211477A patent/GB2104063B/en not_active Expired
- 1982-04-26 SU SU823427200A patent/SU1301316A3/ru active
- 1982-04-26 IE IE976/82A patent/IE52795B1/en unknown
- 1982-04-26 PT PT74796A patent/PT74796B/pt unknown
- 1982-04-26 NO NO821348A patent/NO152875C/no unknown
- 1982-04-26 IL IL65621A patent/IL65621A/xx unknown
- 1982-04-26 GR GR67979A patent/GR75418B/el unknown
- 1982-04-27 JP JP57071130A patent/JPS5835196A/ja active Granted
- 1982-04-27 AU AU83025/82A patent/AU557186B2/en not_active Ceased
- 1982-04-27 ZA ZA822854A patent/ZA822854B/xx unknown
- 1982-04-27 ES ES511753A patent/ES511753A0/es active Granted
- 1982-04-27 CA CA000401740A patent/CA1189070A/en not_active Expired
- 1982-04-27 KR KR8201851A patent/KR870001900B1/ko active
- 1982-04-27 MX MX8210045U patent/MX7260E/es unknown
- 1982-04-27 YU YU00906/82A patent/YU90682A/xx unknown
- 1982-04-27 DK DK188782A patent/DK158472C/da not_active IP Right Cessation
- 1982-04-27 NZ NZ200418A patent/NZ200418A/en unknown
- 1982-04-27 TR TR21241A patent/TR21241A/xx unknown
- 1982-04-28 FI FI821486A patent/FI71159C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS6254436B2 (da)	1987-11-14
IE820976L (en)	1983-02-21
AU8302582A (en)	1983-02-24
EP0073093B1 (en)	1984-10-24
ZA822854B (en)	1983-03-30
NO152875C (no)	1985-12-04
SU1301316A3 (ru)	1987-03-30
TR21241A (tr)	1984-02-07
DE3261037D1 (en)	1984-11-29
IE52795B1 (en)	1988-03-02
JPS5835196A (ja)	1983-03-01
KR830010125A (ko)	1983-12-26
DK158472B (da)	1990-05-21
NO152875B (no)	1985-08-26
DK188782A (da)	1983-02-22
ES8306764A1 (es)	1983-06-01
EP0073093A1 (en)	1983-03-02
DK158472C (da)	1990-10-08
GR75418B (da)	1984-07-16
ATE10003T1 (de)	1984-11-15
FI821486A0 (fi)	1982-04-28
PT74796B (en)	1983-11-07
ES511753A0 (es)	1983-06-01
YU90682A (en)	1985-06-30
PT74796A (en)	1982-05-01
AU557186B2 (en)	1986-12-11
MX7260E (es)	1988-03-01
FI71159B (fi)	1986-08-14
FI821486L (fi)	1983-02-22
CA1189070A (en)	1985-06-18
GB2104063B (en)	1985-11-06
KR870001900B1 (ko)	1987-10-21
NZ200418A (en)	1985-07-12
NO821348L (no)	1983-02-22
GB2104063A (en)	1983-03-02
IL65621A (en)	1985-08-30

Publication	Publication Date	Title
US4405654A (en)	1983-09-20	4'-Halo-substituted sucrose derivatives
US4435440A (en)	1984-03-06	Sweeteners
CA1076110A (en)	1980-04-22	Sweeteners
US4612373A (en)	1986-09-16	Trichloro, 6-substituted sucrose compounds, compositions and uses therefor
FI71159B (fi)	1986-08-14	4'-halogensubstituerade sackarosderivat
JP2005530731A (ja)	2005-10-13	バッファー安定化水性脱アシル化方法
US4473546A (en)	1984-09-25	Brominated sucrose derivatives, compositions and methods of use
JPS6254435B2 (da)	1987-11-14
GB2088855A (en)	1982-06-16	Tetrachlorodisaccharides and their use as sweeteners
JPS6254796B2 (da)	1987-11-17

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: TATE & LYLE PUBLIC LIMITED COMPANY