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Carbohydr Res. 1991 Mar 20;210:221-32.

Synthesis of 3'-deoxy-3'-fluorokanamycin A and 3',4'-dideoxy-3'-fluorokanamycin A.

Author information

1
Institute of Bioorganic Chemistry, Kawasaki, Japan.

Abstract

3'-Deoxy-3'-fluorokanamycin A (14) has been prepared by condensation of 6-azido-2,4-di-O-benzyl-3,6-dideoxy-3-fluoro-alpha-D-glucopyranlsyl++ + bromide (8) and 6-O-(2-O-acetyl-4,6-O-cyclohexylidene-3-deoxy- 3-tosylamino-alpha-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstre ptamine (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.

PMID:
1878879
DOI:
10.1016/0008-6215(91)80124-6
[Indexed for MEDLINE]

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