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

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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Bibliographische Detailangaben
Veröffentlicht in:	Chemical & pharmaceutical bulletin 1987/05/25, Vol.35(5), pp.2136-2139
Hauptverfasser:	Yoshikawa, Masayuki, Torihara, Masahiro, Nakae, Takahiko, Cha, Bae Cheon, Kitagawa, Isao
Format:	Artikel
Sprache:	eng
Schlagworte:	3', 4'-dideoxykanamycin B aminocyclitol aminoglycoside antibiotic Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemical Phenomena Chemistry D-glucosamine D-glucose dibekacin Dibekacin - chemical synthesis Exact sciences and technology Glucosamine Glucose Kanamycin - analogs & derivatives nitromethane cyclization Organic chemistry oxidative decarboxylation Preparations and properties reductive deacetoxylation selective glycosidation
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Beschreibung
Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.35.2136