Article ID Journal Published Year Pages File Type
1389219 Carbohydrate Research 2011 4 Pages PDF
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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
Authors
, , , ,