Synthesis of 3′-deoxy-3′-fluorokanamycin A and 3′,4′-dideoxy-3′-fluorokanamycin A

Add time:07/12/2019    Source:sciencedirect.com

3′-Deoxy-3′-fluorokanamycin A (14) has been prepared by condensation of 6-azido-2,4-di-O-benzyl-3,6-dideoxy-3-fluoro-α-d- glucopyranosyl bromide (8) and 6-O-(2-O-acetyl-4,6-O-cyclohexylidene-3-deoxy-3-tosylamino-α-d-glucopyranosyl)-2-deoxy-1,3-di-N- tosylstreptamine (10). Compound 8 was obtained from 3-deoxy-3-fluoro-1,2:5,6-di-O-isopropylidene-d-glucofuranose in seven steps. 3′,4′-Dideoxy-3′-fluorokanamycin A (22) has been prepared from 12 through selective 4′-chlorodeoxygenation, a key reaction. Both 14 and 22 were more active than 3′-deoxykanamycin A against both sensitive and resistant bacteria.

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