CS272900B1 - Benzyl 2,3-di-c-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranosile)-beta-d-xylopyranoside - Google Patents
Benzyl 2,3-di-c-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranosile)-beta-d-xylopyranoside Download PDFInfo
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- CS272900B1 CS272900B1 CS486689A CS486689A CS272900B1 CS 272900 B1 CS272900 B1 CS 272900B1 CS 486689 A CS486689 A CS 486689A CS 486689 A CS486689 A CS 486689A CS 272900 B1 CS272900 B1 CS 272900B1
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- xylopyranoside
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Abstract
Description
£ V» M.
OS 272900 EL
Vynález sa týká benzyl 2,3-di-0-benzyl-4-0-(2,3,4,6-tetra-0-acetyl- -D-glukopy-ranozyl-β -D-xylopyranozidu.
Benzyl 2-0-(2,3,4-tri-0-acetyl-/ lD-xylopyranozyl)-3,4-di-0-benzyl-/? D-xylopyra-nozid připravili P. Kováč a B, Petrákové /P, Kováč, E. Petráková: Chem. zvěsti 34, 537(1980)/. Doteraz benzyl 2,3-di-0-benzyL-4-0-(2,3,4,6-tetra-0-acetyl-/? -D-glukopyrano-zyl)-^ -B-xylopyranozid nebol připravený. MSže sa použit ako medziprodukt pre přípra-vu sacharidov a ich derivátov.
Podstatou vynálezu je benzyl 2,3-di-0-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-/^ D-glu-kopyranozyl)-/? -D-xylopyranozid vzorca I,
v ktorom R^ znamená benzyl aR2 znamená acetyl. Výhodou benzyl2,3-di-0-benzyl-4-0-(2,3,4,6-tetra-O-acetyl-/ -D-glukopyranozyl)-_ β -D-xylopyranozidu je, že sú chráněné uhlíky 2, 3, 4, 6 na glukopyranózovej jednotkeacetylovými skupinami, uhlíky 1, 2, 3 na xylopyranozovej jednotke benzylovými skupinami,pričom možno substituenty selektívne odstrániť dosahpjúc vysokých výťažkov bez nebezpe-čia porušenía glykozidickej vazby. Příklad 1 K 0,4 g benzyl 2,3-di-O-benzyl-β -D-xylopyranozidu sa přidá 0,36 g kyaniduortuťnatého v 4 ml dichlormetánu a 0,58 g 2,3,4,6-tetra-0-acetyl-í& D-glukopyranozyl-bromxdu a za stálého mieSania sa reakčná zmes udržuje pri teplote 20 °C počas 2 hodin.Potom sa reakčná zmes odfiltruje, dvakrát vytrepe s 50 ml 1 molárneho roztoku bromidudraselného, 50 ml vody, vysuší přidáním bezvodého síranu sodného, odfiltruje a zahusti.Po chromatografickom čistění sa získá 0,56 g (78,9 %) benzyl 2,3-di-0-benzyl~4-0-(2,3,4,6-tetra-0-acetyl-^ -D-glukopyranozyl)-^ -D-xylopyranozidu s teplotou topenia 128,5až 130 °C, po rekryštalizácii z metanolu,Specifická otáčavosť /d/ - 30 0 (c 0,8, chloroform).
Elementárna analýza pre ¢40^46^.4.» mol. hmotnost/750,77: vypočítané: 63,99 hmot. % uhlíka, 6,18 hmot. % vodíka, zistené: 63,89 hmot. % uhlíka, 6,28 hmot. % vodíka.
Benzyl 2,3-di-0-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-/3 D-glukopyranozyl}-/^ -D-xy-lopyranozid može néjsi/ široké použitie akó medzíprodukt pri přípravě 4-0-β -D-gluko-pyranozyl-D-xylopyranózy, ktorá mé použitie v enzýmovej, organickej chémii a na rozli-šeni© druhov mikroorganizmov.
£ V »M.
OS 272900 EL
The present invention relates to benzyl 2,3-di-O-benzyl-4-O- (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl-β-D-xylopyranoside).
Benzyl 2-O- (2,3,4-tri-O-acetyl- [1D-xylopyranosyl) -3,4-di-O-benzyl]? D-xylopyra-nosid prepared by P. Kováč and B, Petrákové / P, Kováč, E. Petráková: Chem. rumors 34, 537 (1980)]. So far, benzyl 2,3-di-O-benzyl-4-O- (2,3,4,6-tetra-O-acetyl- [beta] -D-glucopyranosyl) - [beta] -B-xylopyranoside has not been prepared. MSze is used as an intermediate for the preparation of carbohydrates and their derivatives.
SUMMARY OF THE INVENTION The present invention relates to benzyl 2,3-di-O-benzyl-4-O- (2,3,4,6-tetra-O-acetyl- [D] -glucopyranosyl) -? -D-xylopyranoside of formula I,
wherein R 1 is benzyl and R 2 is acetyl. The advantage of benzyl 2,3-di-O-benzyl-4-O- (2,3,4,6-tetra-O-acetyl- [D-glucopyranosyl] - [beta] -D-xylopyranoside is that they are protected by carbons 2 3, 4, 6 to glucopyranose by monoacetyl groups, carbons 1, 2, 3 to the xylopyranose unit by benzyl groups, wherein the substituents can be selectively removed to yield high yields without the risk of glycosidic bond breach. Example 1 To 0.4 g of benzyl 2,3-di-O-benzyl-β-D-xylopyranoside is added 0.36 g of cyanuric mercuric acid in 4 ml of dichloromethane and 0.58 g of 2,3,4,6-tetra-O -acetyl- & D-Glucopyranosyl Bromoxide is maintained at 20 [deg.] C. for 2 hours with stirring. The reaction mixture is then filtered off, taken up twice with 50 ml of 1 molar solution of potassium bromide, 50 ml of water, dried over sodium sulphate, filtered off and filtered. After chromatographic purification, 0.56 g (78.9%) of benzyl 2,3-di-O-benzyl-4-O- (2,3,4,6-tetra-O-acetyl-4-D) is obtained. -glucopyranosyl) - N -D-xylopyranoside, m.p. 128.5-130 ° C, after recrystallization from methanol, Specific rotation (d / 30 ° C (c 0.8, chloroform).
Elemental analysis for ^40 ^ 46 ^ 4. Mol. mass / 750.77: calculated: 63.99 wt. % carbon, 6.18 wt. % hydrogen, found: 63.89 wt. % carbon, 6.28 wt. % hydrogen.
Benzyl 2,3-di-O-benzyl-4-O- (2,3,4,6-tetra-O-acetyl- [3 D-glucopyranosyl} - N -D-xy-lopyranoside can be used widely) as a product in the preparation of 4-O-β-D-glucopyranosyl-D-xylopyranose, which I use in enzymatic, organic chemistry, and differentiation of microorganisms.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS486689A CS272900B1 (en) | 1989-08-18 | 1989-08-18 | Benzyl 2,3-di-c-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranosile)-beta-d-xylopyranoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS486689A CS272900B1 (en) | 1989-08-18 | 1989-08-18 | Benzyl 2,3-di-c-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranosile)-beta-d-xylopyranoside |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS486689A1 CS486689A1 (en) | 1990-03-14 |
| CS272900B1 true CS272900B1 (en) | 1991-02-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS486689A CS272900B1 (en) | 1989-08-18 | 1989-08-18 | Benzyl 2,3-di-c-benzyl-4-0-(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranosile)-beta-d-xylopyranoside |
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| CS (1) | CS272900B1 (en) |
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1989
- 1989-08-18 CS CS486689A patent/CS272900B1/en unknown
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| CS486689A1 (en) | 1990-03-14 |
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