CS274090B1 - 1,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-beta-d-xylopyranozyl)-beta-d-glucopyranose - Google Patents
1,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-beta-d-xylopyranozyl)-beta-d-glucopyranose Download PDFInfo
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- CS274090B1 CS274090B1 CS491889A CS491889A CS274090B1 CS 274090 B1 CS274090 B1 CS 274090B1 CS 491889 A CS491889 A CS 491889A CS 491889 A CS491889 A CS 491889A CS 274090 B1 CS274090 B1 CS 274090B1
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- Czechoslovakia
- Prior art keywords
- acetyl
- glucopyranose
- beta
- tetra
- tri
- Prior art date
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- 229960002246 beta-d-glucopyranose Drugs 0.000 title abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 3
- 150000002016 disaccharides Chemical class 0.000 abstract description 5
- 244000005700 microbiome Species 0.000 abstract description 3
- 102000004190 Enzymes Human genes 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- NPOKZMNZAPKSBT-LECHCGJUSA-N (2r,3r,4s,5r)-2-bromooxane-3,4,5-triol Chemical compound O[C@@H]1CO[C@H](Br)[C@H](O)[C@H]1O NPOKZMNZAPKSBT-LECHCGJUSA-N 0.000 description 1
- -1 3-D-xylopyranosyl-D-glucopyranose Chemical compound 0.000 description 1
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
- GMIAWATVTRICKZ-IVBFVFLLSA-N beta-D-Xylp-(1->4)-D-Glcp Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O GMIAWATVTRICKZ-IVBFVFLLSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Vynález sa týká l,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-y?-D-xylopyranozyl)-/í,-D-glukopyranózy.
Doteraz nebola připravená l,2,3.6-tetra-O-acetyl-4-O-(2,3,4-tri-O-acetyl-/3-D-xylopyranozyl)-/?.-D-glukopyranóza. Tento derivát disacharidu je medziproduktom pri príprave 4-0-β-D-xylopyranozyl-D-glukopyranózy. 4-0-4-D-Xylopyranozyl-D-glukopyranóza je substrát pre mnohé enzýmy a mikroorganizmy.
Podstatou vynálezu je l,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-^-D-xylopyranozyl)-/3 -D-glukopyranóza vzorca
v ktorom R znamená acetyl. Výhodou tejto organickej zlúčeniny je, že umožňuje jednoduchým sposobom t.j. deacetyláoiou metanolátom sodným pripraviť nový disacharid 4-0-/3-D-xylopyranozyl-D-glukopyranózu. Příklad 1 Κ 1 g l,2,3,6-tetra-0-acetyl-/3-D-glukopyranózy sa přidá 1,5 g kyanidu ortuťnatého v 10 ml acetonitrilu a 2 g 2,3,4-tri-0-acetyl-<>c-D-xylopyranozylbromidu a za stálého miešania sa reakčná zmes udržuje pri teplote 20 °C počas 2 hodin. Potom sa reakčná zmes odfiltruje, zriedi s 50 ml chloroformu, dvakrát vytrepe s 50 ml 1 mol roztokom bromidu draselného a 50 ml vody, vysuší přidáním bezvodého síranu sodného, odfiltruje a zahustí. Po chromatografickom čistění Ba získá 1,13 g 1,2,3,6-tetra-O-acetyl-4-0-(2,3,4-tri~0-acetyl-y$-D-xylopyranozyl)-/3-D-glukopyranózy (65% výtažok), po rekryštalizácii z etanolu s teplotou topenia 160 až 161 °C, Specifickou otáčavostou pčj -36,6° (c 0,86, chloroform).
Elementárna analýza pre θ25^35θ17’ mo·"·· hmotnost’ 606,52: vypočítané: 49,50 hmot. % uhlíka, 5,82 hmot. % vodíka; zistené: 49,51 hmot. % uhlíka, 5,72 hmot. % vodíka. l,2,3,6-Tetra-O-acetyl-4-O-(2,3,4·* tri-0-acetyl-/3 -D- xylopyranozyl)-^-D-glukopyronóza može nájsť široké použitie ako medziprodukt odpovedájúceho disacharidu, který má použitie v enzýmovej a organickej chémii a na rozlišenie mikroorganizmov.
The present invention relates to 1,2,3,6-tetra-O-acetyl-4-O- (2,3,4-tri-O-acetyl-γ-D-xylopyranosyl) -1 H -D-glucopyranose.
To date, 1,2,3,6-tetra-O-acetyl-4-O- (2,3,4-tri-O-acetyl- [3-D-xylopyranosyl) - D -glucopyranose has not been prepared. This disaccharide derivative is an intermediate in the preparation of 4-O-β-D-xylopyranosyl-D-glucopyranose. 4-O-4-D-Xylopyranosyl-D-Glucopyranose is a substrate for many enzymes and microorganisms.
The subject of the invention is 1,2,3,6-tetra-O-acetyl-4-O- (2,3,4-tri-O-acetyl-4-D-xylopyranosyl) - / 3-D-glucopyranose of formula
wherein R is acetyl. The advantage of this organic compound is that it allows the novel 4-O- (3-D-xylopyranosyl-D-glucopyranose) disaccharide to be prepared by simple means, i.e., by deacetylation with sodium methoxide. EXAMPLE 1 1.5 g of 2,3,6-tetra-O-acetyl- [beta] -D-glucopyranose is added with 1.5 g of mercuric cyanide in 10 ml of acetonitrile and 2 g of 2,3,4-tri-O-acetyl The α-xylopyranosylbromide is maintained at 20 ° C for 2 hours while stirring. The reaction mixture is then filtered, diluted with 50 ml of chloroform, shaken twice with 50 ml of 1M potassium bromide solution and 50 ml of water, dried over sodium sulphate, filtered and concentrated. After chromatographic purification of Ba, 1.13 g of 1,2,3,6-tetra-O-acetyl-4-O- (2,3,4-tri-O-acetyl-γ-D-xylopyranosyl) - / 3 is obtained. -D-Glucopyranose (65% yield), after recrystallization from ethanol, m.p. 160-161 ° C, Specific Rotation: -36.6 ° (c 0.86, chloroform).
Elemental analysis for θ25 35 35θ17 mo molar mass 606.52: calculated: 49.50% by weight of carbon, 5.82% by weight of hydrogen found: 49.51% by weight of carbon; % of hydrogen, 1,2,3,6-Tetra-O-acetyl-4-O- (2,3,4 * tri-O-acetyl- [3-D-xylopyranosyl) -4-D-glucopyronose can to find widespread use as a disaccharide-responsive intermediate having uses in enzymatic and organic chemistry and for distinguishing microorganisms.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS491889A CS274090B1 (en) | 1989-08-22 | 1989-08-22 | 1,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-beta-d-xylopyranozyl)-beta-d-glucopyranose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS491889A CS274090B1 (en) | 1989-08-22 | 1989-08-22 | 1,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-beta-d-xylopyranozyl)-beta-d-glucopyranose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS491889A1 CS491889A1 (en) | 1990-08-14 |
| CS274090B1 true CS274090B1 (en) | 1991-04-11 |
Family
ID=5392973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS491889A CS274090B1 (en) | 1989-08-22 | 1989-08-22 | 1,2,3,6-tetra-0-acetyl-4-0-(2,3,4-tri-0-acetyl-beta-d-xylopyranozyl)-beta-d-glucopyranose |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS274090B1 (en) |
-
1989
- 1989-08-22 CS CS491889A patent/CS274090B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS491889A1 (en) | 1990-08-14 |
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