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
- Publication number
- 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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- CS
- 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
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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.
Claims (1)
- PREDMET VYNÁLEZU 1,2,3,6-Tetra-O-acetyl-4-0- (2,3,4- tri-O-acetyl-yS-L-xylopyranozyD-^-D-glukopyranóza vzorca CS 274090 Blv ktorom R představuje acetyl
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 (cs) |
-
1989
- 1989-08-22 CS CS491889A patent/CS274090B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS491889A1 (en) | 1990-08-14 |
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