Syntheses of 6''-Deoxy-6''-fluorokanamycin A, 6''-Deoxy-6''fluoroamikacin, and 1-N-[(R)- and (RS)-3-Amino-2fluoropropanoy]kanamycins

Abstract

As a part of our synthetic studies on fluorine-containing aminoglycoside antibiotics, title compounds have been prepared.6''-Deoxy-6''-fluorokanamycin A and 6''-deoxy-6''-fluoroamikacin were prepared from the corresponding N-benzyloxycarbonyl derivatives of kanamycin A and amikacin, respectively, by use of the DAST reagent.1-N-[(R)- and (R5)-3Amino-2-fluoropropanoyl]kanamycins were prepared by coupling, by use of active esters, of 3-benz yloxycarbonylamino-2-fluoropropanoic acids with 3, 6'-bis(N-benzyloxycarbony1)-3''N-(trifluoroacetyl)kanamycin A. To determine the structures of these compounds 2-D NMR spectroscopies were found to be useful. Since the presence of a fluorine atom causes splitting of the nearby connected ¹H- and ¹³C-signals into a (broad) doublet, the spectra of fluorine-containing compounds facilitate the determination of the structures in the vicinity of the fluorine.