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Carbohydr Res. 1976 Jul;49:141-51.

A synthesis of 3',4'-dideoxykanamycin B.


3',4',-Dideoxykanamycin B, the kanamycin B derivative that is active against resistant bacteria, was prepared from kanamycin B via N-tosylation, 3',4'-O-sulphonylation, 3',4'-unsaturation, and hydrogenation. The unsaturated intermediate was obtained from the 3',4'-di-O-sulphonyl derivatives by the action of sodium iodide in N,N-dimethylformamide; if zinc dust was added in this reaction, aziridine derivatives were formed. Removal of the tosyl group was successfully performed by using sodium in ammonia-ethylamine.

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