Active-latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses

被引：30

作者：

Cao, SD ^{[1
]}

Gan, ZH ^{[1
]}

Roy, R ^{[1
]}

机构：

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

来源：

CARBOHYDRATE RESEARCH | 1999年 / 318卷 / 1-4期

基金：

加拿大自然科学与工程研究理事会;

关键词：

active-latent; glycosylation; 4-nitrophenyl thioglycoside; Lewis X; pentasaccharide;

D O I：

10.1016/S0008-6215(99)00080-4

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：

Glycosylation of 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-beta-D-glucopyranoside with phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3-O-fucosylation with phenyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside using DMTST as promoter afforded the Le(x) trisaccharide intermediate. The latent glycosyl donor was transformed into its active form (p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le(x) pentasaccharide in 71% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：75 / 81

页数：7

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