The Synthesis of Kanamycin Analogs I. α-D-Glucopyranosyl Derivatives of Deoxystreptamine

Abstract

The procedure developed in this laboratory for the synthesis of α-D-glucopyranosides based on the reaction of dimeric tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride with alcohols was employed to synthesize the three α-D-glucopyranosyl deoxystreptamines and 4,6-di-O-α-D-glucopyranosyl deoxystreptamine. Effects of pH change on the n.m.r. spectra of kanamycins A and B and of the above synthetic compounds are interpreted in terms of a conformational change.