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C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

ABSTRACT: The iodocyclization of homoallylic trichloroacetimidates derived from ?-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.

SUBMITTER: Altiti AS

PROVIDER: S-EPMC5240635 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

Altiti Ahmad S AS Mootoo David R DR

Carbohydrate research 20150221

The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000. ...[more]

PMID: 25771297

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