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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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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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.
AbstractList 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.
Author MATSUNO, TOMIO
YONETA, TOSHIO
FUKATSU, SHUNZO
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References 5) T. Tsuchiya, T. Jikihara, T. Miyake, S. Umezawa, M. Hamada, and H. Umezawa, J. Antibiot., 32, 1351 (1979).
6) T. Naito, S. Nakagawa, Y. Abe, K. Fujisawa, and H. Kawaguchi, J. Antibiot., 27, 838 (1974).
1) Part I: T. Yoneta, S. Shibahara, T. Matsuno, S. Tohma, S. Fukatsu, S. Seki, and H. Umezawa, Bull. Chem. Soc. Jpn., 52, 1131 (1979).
2) H. Umezawa, Adv. Carbohydr. Chem. Biochem., 30, 183 (1974); H. Umezawa, "Drug Action and Drug Resistance in Bacteria. II. Aminoglycoside Antibiotics," Univ. Tokyo Press, Tokyo, 1975, p. 211.
8) J.G. Buchanan, J. Chem. Soc., 1958, 2511.
3) S. Umezawa, H. Umezawa, Y. Okazaki, and T. Tsuchiya, Bull. Chem. Soc. Jpn., 45, 3624 (1972
7) T. Nagasawa, K. Kuroiwa, K. Narita, and Y. Isowa, Bull. Chem. Soc. Jpn., 46, 1269 (1973).
T. Miyake, T. Tsuchiya, S. Umezawa, and H. Umezawa, Carbohydr. Res., 49, 141 (1976).
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SubjectTerms 3', 4'-anhydro-4'-epi derivative
Title Deoxygenation of Amino-Glycoside Antibiotics via Anhydro Intermediates. II. Improved Syntheses of 3', 4'-Dideoxykanamycin A and 4'-Deoxykanamycin A
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