Syntheses of 2',3'-dideoxykanamycin A, 2',3'-dideoxyamikacin and related substances.

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2′,3′-Dideoxykanamycin A has been prepared via two ways. 2″-O-Acetyl-4″,6″-O-benzylidene-6′-N,4′-O-carbonyl-1,3,3″-tri-N-tosylkanamycin A was converted to a 2′,3′-unsaturated compound by a modified Tipson and Cohen method. Hydrogenation followed by deblocking gave 2′,3′-dideoxykanamycin A (12). Another route for 12 was through 2′,3′-anhydro-4′,2″,4″,6″-tetra-O-benzoyl-2′-epi-1,3,6′,3″-tetrakis(N-ethoxycarbonyl)kanamycin A (16). Epoxide-ring opening of 16 with hydrogen iodide gave the 3′,2′-iodohydrin, which, after 2′-O-mesylation, led to the 2′,3′-unsaturated compound (19). Deblocking and hydrogenation of 19 gave 12. 2′,3′-Dideoxykanamycin A thus synthesized was led to 2′,3′-dideoxyamikacin and other related compounds by amino protection of 12 other than the 1-amino group by zinc acetate–ethyl trifluoroacetate method followed by 1-N-acyl or 1-urethane formation with appropriate reagents. Their antibacterial activities were described.
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