Semisynthetic aminoglycoside antibacterials. Part I. Preparation of selectively protected garamine derivatives

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Abstract
N-Alkoxycarbonyl and N-acyl derivatives of sisomicin, an unsaturated aminoglycoside antibiotic, have been demonstrated to undergo ready acid-catalysed hydrolysis to the novel pseudodisaccharide garamine [O-(3-deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl)-(1 → 6)-2-deoxy-D-streptamine]. Alternative procedures and routes for the selective protection of various hydroxy-groups in the garamine molecule are discussed. The selectively protected garamine derivatives constitute useful intermediates for the preparation of a wide variety of novel semisynthetic aminoglycoside antibacterials related to the clinically important gentamicins.

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