- Synthesis of 3'-deoxy-3'-fluorokanamycin A and 3',4'-dideoxy-3'-fluorokanamycin A
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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-tosylst
- Takahashi, Yoshiaki,Tsuchiya, Tsutomu,Umezawa, Sumio,Umezawa, Hamao
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p. 221 - 232
(2007/10/02)
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- 3'-fluoro-3'-deoxykanamycin A
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A new compound, 3'-fluoro-3'-deoxykanamycin A is now provided, which is active against gram-negative and gram-positive bacteria, including kanamycin-resistant strains of bacteria and is useful as antibacterial agent for therapeutic treatment of bacterial infections. This new compound is produced by a process comprising reacting a 6-azido-2,4-di-O-protected-3,6-dideoxy-3-fluoro-α-D-glucopyranosyl bromide with the 4-hydroxyl group of a 6-O-(2'-O-protected-3'-N-protected-3'-amino-4',6'-di-O-protected-3'-deoxy-α-D-glucopyranosyl)-1,3-bis-N-protected-2-deoxystreptamine, reducing the azido group of the resulting reaction product into an amino group, and removing the remaining protective groups from the reduction product.
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