78788-41-7Relevant academic research and scientific papers
Synthesis of 4'-deoxy-4'-fluorokanamycin A and B
Takahashi, Yoshiaki,Tsuneda, Sayori,Tsuchiya, Tsutomu,Koyama, Yoshiko,Umezawa, Sumio
, p. 89 - 106 (2007/10/02)
4'-Deoxy-4'-fluorokanamycins A (17) and B (25) have been prepared through fluorinating 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'.
