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Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.

ABSTRACT: Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-beta-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-beta-glycosides in high yield and high selectivity. The high beta-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control.

SUBMITTER: Morris WJ

PROVIDER: S-EPMC2699938 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.

Morris William J WJ Shair Matthew D MD

Organic letters 20090101 1

Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-beta-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-beta-glycosides in high yield and high selectivity. The high beta-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control. ...[more]

PMID: 19061365

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