CS274092B1 - Benzyl 3,4-di-0-benzyl-2-0(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranoside - Google Patents
Benzyl 3,4-di-0-benzyl-2-0(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranoside Download PDFInfo
- Publication number
- CS274092B1 CS274092B1 CS492089A CS492089A CS274092B1 CS 274092 B1 CS274092 B1 CS 274092B1 CS 492089 A CS492089 A CS 492089A CS 492089 A CS492089 A CS 492089A CS 274092 B1 CS274092 B1 CS 274092B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzyl
- acetyl
- beta
- xylopyranoside
- tetra
- 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 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000011541 reaction mixture Substances 0.000 description 2
- -1 Benzyl 3,4-di-O-benzyl-2-O- (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) - β-D-xylopyranoside Chemical compound 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-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
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález ae týká benzyl 3,4-di-0-benzyl-2T0-(2,3,4,6-tetra-O-acatyl-/f-D-glukopyranozyl)-/? -D-xylopyranozldu.
Benzyl 2-0-(2,3,4-tri-0-acetyl-/f-D-xylopyranozyl)-3,4-di-0-benzyl-/J-D-xylopyranozid připravili P. Kováč a E. Petrákové fP. Kováč, E. Petrákovi: Chem, zveati 34, 537 (198O)J . Doteraz benzyl 3,4-di-0-benzyl-2-0-(2,3,4,6-tetra-0-acetyl-/?-D-glukopyranozyl)-/2 -D-xylopyranozid nebol připravený· MÓže sa použif ako medzlprodukt pre pripravu aacharidov a ich derivótov.
Podstatou vynálezu je benzyl 3,4-di-0-benzyl-2-0-(2,3»4,6-tatra-0-acetyl-/í-0-glukopyranozyl)-/?-D-xylopyranozid vzorca
R·^ znamená banzyl a
R2 znamená acetyl.
Výhodou benzyl 3,4-di-0-benzyl-2-0-(2,3,4,6-tetra-0-acatyl-Z?-D-glukopyranozyl)-/<?- 0-xylopyranozidu Je, že sú chráněné uhlíky 2, 3, 4, 6 na glukopyranózovaj jednotka acatylovými skupinami,1 uhlíky 1, 3, 4 na xylpyranózovaj jednotko benzylovými skupinami, pričom ich možno eelektivne odatránif bez nebezpečia porušenia glykozidickej vffzby ziekajúc tak 2-0- 4-D-glukopyranozyl-D-xylopyranózu.
Přiklad 1
K 2 g banzyl 3,4-dl-0-benzyl-/f-D-xylopyranozldu, 1,8 g kyanidu ortufnatáho v 20 ml acetonitrilu aa přidá 2,9 g 2,3,4-tri-O-acetyl-t/z-D-glukopyranozylbromldu a za stálého mieSa nia sa raakčná zmes udržuje pri teplote 40 °C počas 1 hodiny* Poton es reakčná zmes odflltru je, dvakrát vytrepe s 50 ml 1 molárneho roztoku bromidu draselného,' 50 ml vody, vyauSl přidáním bezvodého síranu sodného, odfiltruje a zahusti. Po chromatografickom čistění sa získá 3,05 g (85 %) benzyl 3,'4-di-0-benzyl-2-0-(2,3,4,6-tetra-0-ecetyl-/f-D-glukopyranozyl)- -D-xylopyranozidu, po kryStalizácíi z etanolu a teplotou topenla 89,5 až 90,5 °C, Specifickou otáčavoefou [«ú]q5 - 39,9 0 (c 1, chloroform).
Elementárně analýza pře ·ο1· hmotnosť 750,77:
vypočítaná: 63,99 hmot. % uhlika, 6.18 hmot. % vodika,1.
zistenó: 64,16 hmot. % uhlika, 6,28 hmot. % vodika.
Benzyl 3,4-di-0-benzyl-2-0-{2,3,4,6-tetra-0-acetyl-/J -D-glukopyranozylJ-/d-D-xylopyranozid može nájaf Široké použitie ako medzlprodukt pri přípravě 2-0-/tf-D-glukopyranozyl-O-xylopyranózy, ktorá má použitie v enzýmovej chémli a na rozliSenla druhov mikroorganizmov.
Claims (2)
- PREDMETVYNÁLEZUBenzyl 3,4-dl-0-benzyl-2-0~l2,3,4,6-tetra-0-acetyl-/<3-D- glukopyranozylD-xylopyronozld vzorca v ktoromR| znamená benzyl e R2 znamená acetyl·
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS492089A CS274092B1 (en) | 1989-08-22 | 1989-08-22 | Benzyl 3,4-di-0-benzyl-2-0(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS492089A CS274092B1 (en) | 1989-08-22 | 1989-08-22 | Benzyl 3,4-di-0-benzyl-2-0(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranoside |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS492089A1 CS492089A1 (en) | 1990-08-14 |
| CS274092B1 true CS274092B1 (en) | 1991-04-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS492089A CS274092B1 (en) | 1989-08-22 | 1989-08-22 | Benzyl 3,4-di-0-benzyl-2-0(2,3,4,6-tetra-0-acetyl-beta-d-glucopyranozyl)-beta-d-xylopyranoside |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS274092B1 (sk) |
-
1989
- 1989-08-22 CS CS492089A patent/CS274092B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS492089A1 (en) | 1990-08-14 |
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