SYNTHESES OF METHYL 6-DEOXY-6-HYDROXYAMINO-α-D-GLUCOPYRANOSIDE, 6'-N-HYDROXYKANAMYCIN A, AND 6'-N-HYDROXYDIBEKACIN

Article abstract of DOI:10.1016/0008-6215(85)85196-X

Methyl-6-deoxy-6-hydroxyamino-α-D-glucopyranoside has been prepared from methyl 6-amino-6-deoxy-α-D-glucopyranoside via oxidation with hydrogen peroxide in the presence of sodium tungstate , followed by reduction with sodium cyanoborohydride in an acidic medium.Acetylation of the Z isomer of 2 gave a nitrile derivative.The above oxidation-reduction procedure was applied to kanamycin A and dibekacin, starting from the corresponding 6'-amino-N-tosyl derivatives.On treatment with sodium in liquid ammonia, 6'-deamino-6'-hydroxyimino-1,3,3''-tri-N-tosylkanamycin A gave the corresponding N-detosyl derivative in good yield with the 6'-aldoxime group remaining intact, but, with 6'-deamino-6'-hydroxyimino-1,3,2',3''-tetra-N-tosyldibekacin, the N-detosyl derivative (17) was obtained only by a very short reaction period.The antibacterial activities of 17 and 6'-N-hydroxydibekacin were demonstrated.