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The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000

Author:
Altiti, Ahmad S., Bachan, Stewart, Mootoo, David R.
Source:
Organic letters 2016 v.18 no.18 pp. 4654-4657
ISSN:
1523-7052
Subject:
aldehydes, ceramides, chemical reactions, chemical structure
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.
Agid:
5791741