Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.
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.
Morris
William J
WJ
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Shair
Matthew D
MD
D000478:Alkylation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008968:Molecular Conformation; D013237:Stereoisomerism
D006027:Glycosides