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Carbohydr Res. 1992 Jul 20;232(1):89-105.

Synthesis of 4'-deoxy-4'-fluorokanamycin A and B.

Author information

1
Institute of Bioorganic Chemistry, Kawasaki, Japan.

Abstract

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'.

PMID:
1423353
DOI:
10.1016/s0008-6215(00)90996-0
[Indexed for MEDLINE]

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