Direct vinylation of glucose derivatives with acetylene

被引：14

作者：

Trofimov, Boris A. ^{[1
]}

Parshina, Lidiya N. ^{[1
]}

Oparina, Ludmila A. ^{[1
]}

Tantsyrev, Anatolii P. ^{[1
]}

Khil'ko, Marina Ya. ^{[1
]}

Vysotskaya, Oksana V. ^{[1
]}

Stepanov, Andrey V. ^{[1
]}

Gusarova, Nina K. ^{[1
]}

Henkelmann, Jochem ^{[2
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

[2] BASF AG, Ammonia Laab ZAR C, D-67056 Ludwigshafen, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 47期

关键词：

glucose derivatives; acetylene; vinyl ethers; superbase catalytic systems;

D O I：

10.1016/j.tet.2007.08.107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl ethers, promising chiral carbohydrate synthons, have been synthesized by the addition of glucose acetals (1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose, methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, 1,2-O-cyclohexylidene-alpha-D-glucofuranose, methyl alpha-D-glucopyranoside) to acetylene under atmospheric and elevated pressures in an autoclave in the presence of superbase catalytic systems (KOH-DMSO, t-BuOK-DMSO). The complete vinylation of 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose and methyl alpha-D-glucopyranoside has been realized under elevated pressure of acetylene in the system KOH-THF as well. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：11661 / 11665

页数：5

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