title: 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.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
authors.forename: William J
authors.initials: WJ
authors.lastname: Morris
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Shair
mesh_terms: D000478:Alkylation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D006027:Glycosides