Synthesis of 4′-deoxy-4′-fluorokanamycin A and B

Add time:07/19/2019    Source:sciencedirect.com

4′-Deoxy-4′-fluorokanamycins A (17) and B (25) have been prepared through fluorinative ring-opening of the d-galacto-3′,4′-oxiranes (8 and 21) derived from kanamycin A and B with potassium hydrogenfluoride in ethane-1,2-diol. The mechanism of preponderant formation of the 4′-deoxy-4′-fluoro-d-gluco (9 and 22) over the 3′-deoxy-3′-fluoro-d-gulo derivatives was discussed. In the synthesis of 25, the unusual 3′,6′-epimine (23) was the main product along with the 4′-deoxy-4′-fluoro derivative. The mechanism of this reaction is also discussed. Both 17 and 25 were active against resistant bacteria producing aminoglycoside-adenylylating enzymes for HO-4′.

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