Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines

被引：47

作者：

Boullanger, P ^{[1
]}

Maunier, V ^{[1
]}

Lafont, D ^{[1
]}

机构：

[1] Univ Lyon 1, UMR CNRS 5622, Lab Chim Organ 2, Chim Phys Elect, F-69622 Villeurbanne, France

来源：

CARBOHYDRATE RESEARCH | 2000年 / 324卷 / 02期

关键词：

glycosyl azides; glycosylamides; triphenylphosphine; acyl chlorides; Staudinger reaction;

D O I：

10.1016/S0008-6215(99)00284-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Protected glycosyl azides react with acyl chlorides in the presence of triphenylphosphine to afford glycosylamides in high yields, at room temperature. Starting from the P-glycosyl azides, the reaction is highly stereoselective and occurs with retention of configuration, whereas the a-azido anomers display a lower stereoselectivity giving rise to alpha/beta mixtures of glycosylamides. The reaction was applied to several monosaccharidic azides and to lactosyl azide with various acyl chlorides; it was shown to be of general use for preparing 1,2-trans beta-glycosylamides. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：97 / 106

页数：10

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