Glycosylation of N-acetylglucosamine:: Imidate formation and unexpected conformation

被引：48

作者：

Liao, L ^{[1
]}

Auzanneau, FI ^{[1
]}

机构：

[1] Univ Guelph, Dept Chem & Biochem, Guelph, ON N1G 2W1, Canada

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 15期

关键词：

D O I：

10.1021/ol034669x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Rhamnosylation in mild conditions of a disaccharide containing N-acetylglucosamine afforded the imidate 6 while at higher temperature and concentration of promoter trisaccharide 7 was isolated. The kinetic imidate 6 was independently rearranged in 50% yield to the thermodynamic trisaccharide 7. Comparative NMR studies of 7 in CDCl3 and DMSO-d(6) suggest the formation of a nonchair conformation in CDCl3. The structure of 7 was confirmed through the independent synthesis of the N-acetylacetamido trisaccharide 11.

引用

页码：2607 / 2610

页数：4

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