Regiospecific syntheses of N-acetyllactosamine derivatives and application toward a highly practical synthesis of Lewis X trisaccharide

被引：36

作者：

Gan, ZH ^{[1
]}

Cao, SD ^{[1
]}

Wu, QQ ^{[1
]}

Roy, R ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1999年 / 18卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1080/07328309908544034

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：

An efficient methodology for regiospecific glycosylation was developed by using 6-O-tert-butyldiphenylsilyl N-acetylglucosamine derivatives 3 and 5 which bear two free hydroxyl groups as accepters. The regiospecificity was attributed to the presence of the tert-butyldiphenylsilyl group at the O-6 position of the N-acetylglucosamine derivatives. Glycosylation of suitably protected galactoside donors 10-14 with accepters 3 and 5 gave only beta (1-->4) linked disaccharides 15-19 in good yields. Fucosylation of disaccharide 18 led to Lewis X (Le(x)) trisaccharide 21 in high yield.

引用

页码：755 / 773

页数：19

共 23 条

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