Spectinomycin modification. IV. The synthesis of 3'-aminomethyldihydrospectinomycins via spectinomycin 3'-cyanohydrins.
The C-3'-carbonyl group of N-protected spectinomycin is converted into the corresponding aminomethylalcohols via the intermediacy of cyanohydrins. Methodology for the selective synthesis of either epimer with retention of protection in the aminocyclitol ring provides valuable synthetic intermediates for the preparation of analogs of this important antibiotic. The new methodology provides an efficient synthesis of the highly active 3'-aminomethyldihydrospectinomycins.
Thomas
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Infectious Diseases Research, Upjohn Company, Kalamazoo, Michigan 49001.
Fritzen
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D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000138:chemical synthesis* / Q000494:pharmacology; D000198:Spectinomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
D009570:Nitriles; C057888:3'-aminomethyldihydrospectinomycin; C057887:N,N'-dibenzyloxycarbonyl-3'-spectinomycin cyanohydrin; D000198:Spectinomycin