The reaction of ammonia with acylated disaccharides. Part IX. Acetyl derivatives of melibiose

Abstract

The reaction of methanolic or aqueous ammonia with octa-O-acetyl-β-melibiose gives N-acetyl-6-O-α-D-galactopyranosyl-β-D-glucofuranosylamine (I) and 1,1-bis(acetamido)-1-deoxy-6-O-α-D-galactopyranosyl-D-glucitol (IV). The structure of the furanoid compound was demonstrated by oxidation with periodate. The factors which determine the different yields of these products in both media are discussed and the yields are compared with those of nitrogenated products obtained by ammonolysis of acetates of 1,4-linked disaccharides.