CS272899B1 - Benzyl 2,4-di-o-benzyl-3-o(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranozide - Google Patents
Benzyl 2,4-di-o-benzyl-3-o(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranozide Download PDFInfo
- Publication number
- CS272899B1 CS272899B1 CS492189A CS492189A CS272899B1 CS 272899 B1 CS272899 B1 CS 272899B1 CS 492189 A CS492189 A CS 492189A CS 492189 A CS492189 A CS 492189A CS 272899 B1 CS272899 B1 CS 272899B1
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- CS
- Czechoslovakia
- Prior art keywords
- benzyl
- acetyl
- tetra
- beta
- glucopyranosyl
- Prior art date
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title claims abstract description 15
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- 150000001720 carbohydrates Chemical class 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- -1 3-O-β-D-glucopyranosyl-D-xylopyranose Chemical compound 0.000 description 3
- 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
- 235000014633 carbohydrates Nutrition 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
- 239000011541 reaction mixture Substances 0.000 description 2
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
(57)syntetizovaný disacharid benzyl 2,4-diO-benzyl-3-O-(2,3,4,6-tetra-0-acetyl-(i- -D-glukopyranozyl)- β -D-xylopyranozid vzorca, v ktorom R1 znamená benzyl a Rj? znamená acetyl, je určený na přípravy 3-0-β -D-glukopyranozyl-D-xylopyranozy ako medziprodukt. Riešenie mé použitie v chémii saoharidov a organiokej chémii.
(Π) 272 899 (13) Bj.
(51) lni. CL5
C 07 H 15/00
CS 272899 EL
Vynález sa týká benzyl 2,4-di-0-benzyl-3-0-(2,3,4,6-tetra-0-acetyl-^ -D-glukopyranozyl )-^ -D-xylopyranozidu.
Benzyl 2-0-(2,3,4-tri-0-acetyl-/? -D-xylopyranozyl)-3,4-di-0-benzyl-/í’ -D-xylopyranozid připravili P. Kováč a E. Petrákové /P. Kováč, E. Petrákové; Chem. zvěsti 34, 537 (1980)/. Doteraz benzyl 2,4-di-0-benzyl-3-0-(2,3,4,6-tetra-0-acetyl-/ -D-glukopyranozyl)-/3 -D-xylopyranozid nebol připravený. Može sa použit? ako medziprodukt pre přípravu sacharidov a ich sacharidov.
Podstatou vynálezu je benzyl 2,4-di-0-benzyl-3-0-(2,3,4,6-tetra-0-acetyl-/ď -D-glukopyranozyl)- β -D-xylopyranozid vzorca
v ktorom znamená benzyl a H2 znamená acetyl.
Výhodou benzyl 2,4-di-0-benzyl-3-0-(2,3,4,6-tetra-0-acetyl-β -D-glukopyranozyl)-β -D-xylopyranozidu je, že sú chráněné uhlíky 2, 3, 4, 6 na glukopyranózovej jednotke acetylovými skupinami, uhlíky 1, 3, 4 na xylopyranózovej jednotke benzylovými skupinami, pričom ich možno selektívne odstrániť bez nebezpečia porušenia glykozidickej vazby získajúc tak 3-0-/? -D-glukopyranozyl-D-xylopyranózu.
Příklad 1
K 1 g benzyl 2,4-di-O-benzyl-^ -D-xylopyranozidu, 0,9 g kyanidu ortuťnatého-v 10 ml acetonitrilu sa přidá 1,48 g 2,3,4,6-tetra-0-acetyl-oC-D-glukopyranozylbromidu a za stálého miešania sa reakčná zmes udržuje pri teplote 40 °C počas 2 hodin. Potom sa reakčná zmes odfiltruje, dvakrát'· premyje 40 ml chloroformu, dvakrát vytrepe s 50 ml 1 molárneho roztoku bromidu draselného, 50 ml vody, vysuší přidáním bezvodého síranu sodného, odfiltruje a zahustí. Po chromatografickom čistění sa získá 1,5 g (84,3 %) benzyl 2,4-di-0-benzyl-3-0-(2,3,4,6-tetra-0-acetyl-/? -D-glukopyranozyl)- 0-D-xylopyranozidu so Specifickou otáčavosťou /dj - 18 0 (c 1, chloroform),
Elementárna analýza pre mol. hmotnosť 750,77:
vypočítané: 63,99 hmot, % uhlíka, 6,18 hmot. % vodíka, zistené: 64,20 hmot. % uhlíka, 6,21 hmot. % vodíka,
Benzyl Ž^-di-O-benzyl-B-O-ÍS^^jS-tetra-O-acetyl-/^ -D-glukopyranozyl)-^ -D-xylopyranozid može náj sť široké použitie ako medziprodukt pri přípravě 3-0- β -D-glukopyranozyl-D-xylopyranózy, ktorá má použitie v enzýmovej chémii a na rozlíšenie druhov mikroorganizmov.
Claims (1)
- PREDMET VYNÁLEZUBenzyl 2,4-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl- /3 -xylopyranozid vzorea-D-glukopyranozyl)- β -D- v ktoromR1 znamená benzyl a R2 znamená acetyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS492189A CS272899B1 (en) | 1989-08-22 | 1989-08-22 | Benzyl 2,4-di-o-benzyl-3-o(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranozide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS492189A CS272899B1 (en) | 1989-08-22 | 1989-08-22 | Benzyl 2,4-di-o-benzyl-3-o(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranozide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS492189A1 CS492189A1 (en) | 1990-06-13 |
| CS272899B1 true CS272899B1 (en) | 1991-02-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS492189A CS272899B1 (en) | 1989-08-22 | 1989-08-22 | Benzyl 2,4-di-o-benzyl-3-o(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranozide |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS272899B1 (cs) |
-
1989
- 1989-08-22 CS CS492189A patent/CS272899B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS492189A1 (en) | 1990-06-13 |
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