Synthesis of 2''-acylamido derivatives of 2''-amino-5,2''-dideoxy-5-epi-5-fluorodibekacin and a study on the structures of 5-fluorinated dibekacin analogs by C-13 NMR

Several 2 ''-amino-2 ''-deoxy and 2 ''-acylamido-2 ''-deoxy derivatives (15-21) of 5-deoxy-5-epi-5-fluorodibekacin have been prepared, introducing the 2 ''-NH2, up via oxidation-methoxyimination-reduction processes. The C-4 and C-6 chemical shifts in the C-13 NMR spectra of several 5-fluorinated kanamycin analogs have been studied, and the difference in shifts was explained on the basis of F-5-O-4 and F-5-O-6 distances estimated by MOPAC93/PM3 calculations on related model compounds. (C) 1997 Elsevier Science Ltd.