Abstract
A diastereoisomer of Kanamycin C has been synthesized by a modified Koenigs—Knorr reaction of 3,4,6-tri- O-acetyl-2-(2,4-dinitroanilino)-2-deoxy-α- D-glucopyranosyl bromide with 4- O-(3-acetamido-2,4,6-tri- O-benzyl-3-deoxy-α- D-glucopyranosyl)- N,N′-di[(benzyloxy)carbonyl]-2-deoxystreptamine. Several Kanamycin analogues were synthesized by a similar condensation reaction. Each of the condensed products was isolated as its crystalline tetra- N-acetyl derivative and was proved by n.m.r. spectroscopy in D 2O to have the α-configuration.
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