Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent S n2 reaction

Abstract

Benzylthioalkyl glycosides of d-glucuronic acid, N-acetyl- d-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent S n2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields.