DEOXY DERIVATIVES OF BUTIROSIN A AND 5"-AMINO-5"-DEOXYBUTIROSIN A, AMINOGLYCOSIDE ANTIBIOTICS RESISTANT TO BACTERIAL 3'-PHOSPHORYLATIVE ENZYMATIC INACTIVATION SYNTHESIS AND NMR STUDIES

Abstract

3'-Deoxybutirosin A (4), 5"-amino-3', 5"-dideoxybutirosin A (6), and 5"-amino-4', 5"-dideoxybutirosin A (7) were prepared by deoxygenation of the appropriate hydroxyl in suitably protected derivatives of butirosin A, using sequentially trifluoromethylsulfonylation, displacement with benzenethiolate, and hydrogenolysis. The structures of the compounds were confirmed by NMR spectroscopy, using ¹³C NMR and ¹H NMR at up to 600 MHz. The compounds are broad-spectrum antibiotics active against resistant microorganisms which i n activate butirosin and related aminoglycosides by 3'-phosphorylation.