A total synthesis of the methyl glycoside of ganglioside GM1

被引：31

作者：

Bhattacharya, SK

Danishefsky, SJ

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

[2] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 01期

关键词：

D O I：

10.1021/jo9912496

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the methyl glycoside of GM(1) (1b) has been accomplished. The key step in the synthesis involves the sulfonamidoglycosidation reaction, which is used to create a beta-linkage leading to a GaINAc residue joined to the C4 hydroxyl group of a galactose unit of a C3 sialylated lactosyl moiety. The "proximal hydroxyl" directing effect, which has been postulated before, manifests in this context as well leading to the preponderant formation of the beta-glycoside. Together with asialo GM(1) and other substructures, the GM(1) methyl glycoside has been submitted for biological assays as potential ligands for bacterial and viral infection sites.

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页码：144 / 151

页数：8

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