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.
D003982:Dibekacin / Q000138:chemical synthesis*; D007612:Kanamycin / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation
D003982:Dibekacin; D007612:Kanamycin