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Deoxysugar synthesis. IV. Deoxygenation of aminoglycoside antibiotics through reduction of their dithiocarbonates.

1978; Pharmaceutical Society of Japan; Volume: 26; Issue: 6 Linguagem: Inglês

10.1248/cpb.26.1786

1347-5223

Teruo Hayashi, Teiki Iwaoka, Noriko Takeda, Eiji Ohki,

Microbial Natural Products and Biosynthesis

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.