Highly efficient stereospecific preparation of Tn and TF building blocks using thioglycosyl donors and the Ph2SO/Tf2O promotor system

被引：41

作者：

Cato, D ^{[1
]}

Buskas, T ^{[1
]}

Boons, GJ ^{[1
]}

机构：

[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30603 USA

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2005年 / 24卷 / 4-6期

基金：

美国国家卫生研究院;

关键词：

glycosylation; thioglycoside; Tn antigen; TF antigen; glycopeptide;

D O I：

10.1081/CAR-200067091

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：

The activation of 2-azido-2-deoxy Tn and TF thioglycosyl. donors by the powerful thiophilic promoter system Ph2SO/Tf2O has been investigated. Glycosylation of an Fmoc-protected threonine derivative gave 1,2-cis glycosides in high yields and excellent stereoselectivities. The galactosylation of phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-beta--galactopyranoside was achieved in high yield and without orthoester formation using a trichloroacetimidate donor carrying a 2-O-(2,5-difluorobenzoyl) group. The anomeric thiophenyl group of the constructed TF disaccharide could directly be activated by the van Boom promotor for the glycosylation of a threonine derivative.

引用

页码：503 / 516

页数：14

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