Deoxygenation of Amino-Glycoside Antibiotics via Anhydro Intermediates. II. Improved Syntheses of 3', 4'-Dideoxykanamycin A and 4'-Deoxykanamycin A

A new deoxygenation of kanamycin A leading to 3', 4'-dideoxykanamycin A and 4'-deoxykanamycin A is described. The key stage in the syntheses involves the formation of the 3', 4'-anhydro-4'-epi derivative (5) followed by its conversion to the 3'Δ and 4'-deoxy d...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 29; no. 12; pp. 3464 - 3468
Main Authors YONETA, TOSHIO, MATSUNO, TOMIO, FUKATSU, SHUNZO
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 1981
Subjects
3', 4'-anhydro-4'-epi derivative
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Summary:A new deoxygenation of kanamycin A leading to 3', 4'-dideoxykanamycin A and 4'-deoxykanamycin A is described. The key stage in the syntheses involves the formation of the 3', 4'-anhydro-4'-epi derivative (5) followed by its conversion to the 3'Δ and 4'-deoxy derivative through the iodohydrin. Compound 5 was prepared by the treatment of 2', 3', 2"-tri-O-benzoyl-4", 6"-O-cyclohexylidene-4'-O-methylsulfonyl-tetra-N-tert-butyloxycar-bonylkanamycin A (4) with sodium methoxide.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.29.3464