The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2016 Aug 26

PMID 27560147

Citations 4

Authors

Ahmad S Altiti

Stewart Bachan

David R Mootoo

Affiliations

Soon will be listed here.

Abstract

A synthesis of glycosphingolipids that centers on the reaction of O- and C-glycosyl crotylstannanes and relatively simple lipid aldehydes is described. The modularity of this strategy and versatility of the crotylation products make this an attractive approach to diverse, highly substituted libraries. The methodology is applied to analogues of the potent imunostimulatory glycolipid KRN7000, including O-, methylene-, and fluoromethine-linked isosteres with diastereomeric ceramide segments and 2-amido substitutes.

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