Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1389219 | Carbohydrate Research | 2011 | 4 Pages |
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
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Sergey S. Pertel, Oksana A. Gorkunenko, Elena S. Kakayan, Vasily Ja. Chirva,