Synthesis of 3'-deoxy-3'-fluorokanamycin A and 3',4'-dideoxy-3'-fluorokanamycin A.
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.
Takahashi
Y
Y
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuchiya
T
T
Umezawa
S
S
Umezawa
H
H
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D007612:Kanamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D015394:Molecular Structure
D000900:Anti-Bacterial Agents; C046895:3'-deoxy-3'-fluorokanamycin A; C070508:3',4'-dideoxy-3'-fluorokanamycin A; D007612:Kanamycin