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The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.

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.

SUBMITTER: Altiti AS

PROVIDER: S-EPMC5721664 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.

Altiti Ahmad S AS Bachan Stewart S Mootoo David R DR

Organic letters 20160825 18

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-a ...[more]

PMID: 27560147

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