Aminosaccharides. Part III. Acid hydrolysis of 6-O-(2-amino-2-deoxy-α[and β]-D-glucopyranosyl)-D-galactose hydrochloride and its N-acetyl and N-2,4-dinitrophenyl derivatives

Abstract

Alkyl glycosides of 2-deoxy-2-(2,4-dinitroanilino)-D-glucopyranose are hydrolysed by 3N-acid to yield 2-deoxy-2-(2,4-dinitroanilino)-D-glucose. The disaccharides 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-glactose hydrochloride and its β-anomer are hydrolysed very slowly by 3N-acid. Acid hydrolysis of the biosidic linkages of the N-acetyl derivatives of the disaccharides is initially rapid, but is prolonged by concurrent deacylation; acid hydrolysis of the N-2,4-dinitrophenyl derivatives is rapid, and proceeds with no loss of the N-substituent.