Efficient Syntheses of a Series of Glycosphingolipids with 1,2‐trans‐Glycosidic Linkages

Abstract

A series of glycosphingolipids with 1,2‐trans‐glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido‐sphingosine as the glycosyl acceptor. During the preparation of the target compounds, it was found that the α‐L‐arabinopyranosyl unit in target 7e and intermediates 7b–7d existed in the ¹ C ₄ conformation and that the β‐L‐fucopyranosyl unit in 10e adopted the ⁴ C ₁ conformation.

Keywords:

• Glycosphingolipid with 1,2‐trans‐glycosidic linkage
• Schmidt's
• glycosyl trichloroacetimidate
• Azido‐sphingosine
• Glycosylation
• Conformation

Acknowledgments

This work is supported by the National Basic Research Program of China (2003CB716400).