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Org Lett. 2009 Jan 1;11(1):9-12. doi: 10.1021/ol8022006.

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

Author information

1
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.

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.

PMID:
19061365
PMCID:
PMC2699938
DOI:
10.1021/ol8022006
[Indexed for MEDLINE]
Free PMC Article

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