Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Deoxygenation of Amino-Glycoside Antibiotics via Anhydro Intermediates. II. Improved Syntheses of 3', 4'-Dideoxykanamycin A and 4'-Deoxykanamycin A
TOSHIO YONETATOMIO MATSUNOSHUNZO FUKATSU
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1981 Volume 29 Issue 12 Pages 3464-3468

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Abstract
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.
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© The Pharmaceutical Society of Japan
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