Chemical modification of aminoglycosides. 3. Synthesis of 2"-deoxykanamycins from neamine.
The preparation of 2"-deoxykanamycin B (12) and 2",3',4'-trideoxykanamycin B (14) from neamine (1) is described. Key intermediates in the synthesis of these 2"-deoxyaminoglycoside antibiotics are 3',4'-bis-O-(p-nitrobenzoyl)-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (6) and 3',4'-dideoxy-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (9). The amino groups of these intermediates are blocked by the trifluoroacetyl group, a blocking group not widely used in aminoglycoside chemistry.
D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D007612:Kanamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D009355:Neomycin
D007612:Kanamycin; D009355:Neomycin