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 13C NMR

Article abstract of DOI:10.1016/S0008-6215(97)00031-1

Several 2N-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 group via oxidation-methoxyimination-reduction processes. The C-4 and C-6 chemical shifts in the ¹³C 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.