Studies of Aminosugars. XX. The Synthesis of 6-O-(3-Amino-3-deoxy-α- d -glucopyranosyl)-2-deoxystreptamine

Abstract 6-O-(3-Amino-3-deoxy-α-d-glucopyranosyl)-2-deoxystreptamine (3AD) which is a glycoside component of kanamycin A has been synthesized. Amino and hydroxyl groups of 2-deoxystreptamine were masked with carbobenzoxy and isopropylidene groups to give racemic mono-O-isopropylidene-di-N,N′-carbobenzoxy-2-deoxystreptamine with which 3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-d-glucopyranosyl chloride was condensed by a modified Koenigs-Knorr reaction. Removal of all the masking groups followed by N-dinitrophenylation, acetylation and chromatography gave the product identical with an authentic specimen of the penta-O-acetyl-tri-N-(2,4-dinitrophenyl) derivative of the natural 3AD. The synthetic product was further led to 3AD identical with a natural sample.