M. Kugelman, A. Mallams, H. F. Vernay
1976
Citations
0
Influential Citations
7
Citations
Journal
Journal of the Chemical Society. Perkin transactions 1
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.