Studies of Antibiotics and Related Substances. XXXII. Syntheses of Neamine and Its Analogue

Neamine, an antibiotic glycoside, was synthesized from paromamine. The preferential tosylation of the primary hydroxyl group of tri-N-acetylparomamine was followed by the replacement of the tosyloxy group with an azido group. The azido derivative was catalytically hydro-genated and acetylated to give 4-O-(2,6-diacetamido-2,6-dideoxy-α-d-glucopyranosyl)-N, N-diacetyldeoxystreptamine. De-N-acetylation of the product gave neamine. Furthermore, a structural isomer of neamine, namely 6-O-(3,6-diamino-3,6-dideoxy-α-d-glucopyranosyl)-deoxystreptamine, was synthesized from 6-O-(3-amino-3-deoxy-α-d-glucopyranosyl)-deoxystrept amine which was obtained from kanamycin by partial hydrolysis.