Glycosides of 1-amino-1-deoxy-D-fructose

Article abstract of DOI:10.1016/0008-6215(90)84258-V

A general procedure for the preparation of alkyl 1-amino-1-deoxy-α-D-fructofuranosides is described. 1-Amino-1-deoxy-D-fructose (acetate salt) was transformed into several N-<1-(2-acylvinyl)>- and N-<1-(2,2-diacylvinyl)>derivatives.Fisher glycosidation of these compounds with various alcohols yielded mixtures of the corresponding alkyl α- and β-D-fructofuranosides in which the α anomers preponderated (35-60percent).N-Deprotection of the latter compounds afforded the alkyl 1-amino-1-deoxy-α-D-fructofuranosides in yields of 75-95percent.