Department of Organic and Biological Chemistry, V.I. Vernadsky Taurida National University, Vernadsky ave. 4, Simferopol, Crimea 95007, Ukraine
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.