Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: a broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent SN2 reaction.
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 SN2 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.
Matsuoka
K
K
Department of Functional Materials Science, Faculty of Engineering, Saitama University, Urawa, Japan. koji@fms.saitama-u.ac.jp
Kurosawa
H
H
Esumi
Y
Y
Terunuma
D
D
Kuzuhara
H
H
D000577:Amides / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D013457:Sulfur Compounds / Q000737:chemistry
D000577:Amides; D002264:Carboxylic Acids; D009005:Monosaccharides; D013457:Sulfur Compounds; D000641:Ammonia