title: Synthesis of 1,2-cis- and 1,2-trans-glycosides of 2-acetamido-4,6-O-benzylidene-2-deoxy-D-glucopyranose by anomeric O-alkylation.
abstract: The reaction of a partially protected 1-hydroxy derivative of N-acetyl-D-glucosamine with benzyl bromide under conditions of anomeric O-alkylation was studied. It was found that the stereoselectivity of the reaction depended on the nature of the alkali metal cation constituent of a transient ion pair. The substitution of the Li(+) cation for K(+) or complexation with a crown ether allowed the steric outcome to be shifted from β- to α-selectivity.
authors.affiliation: Department of Organic and Biological Chemistry, V.I. Vernadsky Taurida National University, Vernadsky ave. 4, Simferopol, Crimea 95007, Ukraine. orgchem@crimea.edu
authors.forename: Sergey S
authors.initials: SS
authors.lastname: Pertel
authors.forename: Oksana A
authors.initials: OA
authors.lastname: Gorkunenko
authors.forename: Elena S
authors.initials: ES
authors.lastname: Kakayan
authors.forename: Vasily Ja
authors.initials: VJ
authors.lastname: Chirva
mesh_terms: D000478:Alkylation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006027:Glycosides