SYNTHESIS OF DIBEKACIN (3', 4'-DIDEOXYKANAMYCIN B) FROM D-GLUCOSAMINE AND D-GLUCOSE

Masayuki Yoshikawa; Masahiro Torihara; Takahiko Nakae; Bae Cheon Cha; Isao Kitagawa

doi:10.1248/cpb.35.2136

Masayuki Yoshikawa, Masahiro Torihara, Takahiko Nakae, Bae Cheon Cha, Isao Kitagawa

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Keywords: dibekacin, 3', 4'-dideoxykanamycin B, aminoglycoside antibiotic, aminocyclitol, D-glucosamine, D-glucose, nitromethane cyclization, oxidative decarboxylation, reductive deacetoxylation, selective glycosidation

JOURNAL FREE ACCESS

1987 Volume 35 Issue 5 Pages 2136-2139

DOI https://doi.org/10.1248/cpb.35.2136

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Abstract

An aminoglycoside antibiotic, dibekacin (=3', 4'-dideoxykanamycin B) (22), has been synthesized from D-glucosamine and D-glucose using an oxidative decarboxylation reaction with lead tetraacetate and a reductive deacetoxylation reaction with sodium borohydride as keyreactions.

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