Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

被引：48

作者：

Tanaka, H ^{[1
]}

Adachi, M ^{[1
]}

Takahashi, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 07期

关键词：

glycosyl amino acids; one-pot glycosylation; glycopeptides; glycosyl fluorides; oligosaccharide;

D O I：

10.1016/j.tetlet.2003.12.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl anther. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1433 / 1436

页数：4

共 43 条

[1] Intermolecular aglycon transfer of a phenyl 1-thiogalactosaminide derivative under trichloroacetimidate glycosylation conditions [J].