T. Hayashi, T. Iwaoka, N. Takeda
Jun 25, 1978
Citations
0
Influential Citations
42
Citations
Journal
Chemical & pharmaceutical bulletin
Abstract
3-Dithiocarbonates (1d, 1e, 3a) and 3, 4-bis analog (1b) derived from methyl 2, 6-dibenzyloxycarbonylamino-2, 6-dideoxy-α-D-glucopyranoside (1a) were converted into 3-deoxy compounds (1c, 1f, 3b) and 3-eno compound (2) respectively in good yield on treatment with tributylstannane. This reaction process was extended into the field of aminoglycoside antibiotics, giving 5-deoxykanamycin B (8a), 3', 4', 5-trideoxykanamycin B (8c), 3', 4', 5-trideoxy-3'-enokanamycin B (8b), 6-deoxybutirosin A (9a), and 3'-deoxybutirosin A (9b) whose antibacterial activities were discussed. Structures of these deoxysugars were confirmed by carbon-13 nuclear magnetic resonance spectrometry.