ChemInform Abstract: Synthesis of 3′,4′,6′-Trideoxy-6′-fluorokanamycin C, 3′,4′-Dideoxy-6′- C-(fluoromethyl)kanamycin B, and Their 1-N-((S)-4-Amino-2- hydroxybutanoyl) Derivatives.

Abstract

3′,4′,6′-Trideoxy-6′-fluorokanamycin C (5) has been prepared by treatment of a protected kanamycin C derivative having the free 6-hydroxyl group with DAST, as the key step. Two 3′,4′-dideoxy-6′-C-(fluoromethyl)kanamycin B′s (17a and 17b) have been prepared from a 5′-C-aldehyde derivative of kanamycin C through a sequence of reactions involving nitromethane condensation and 6′,7′-(N-tosylepimino)-ring opening with KHF2, as the key steps. 1-N-[(S)-4-Amino-2-hydroxybutanoyl] derivatives of 5 and 17a were prepared by coupling of the [(S)-4-amino-2-hydroxybutanoyl] residue to the 1-amino group of 5 and 17a by utilizing the zinc acetate-ethyl trifluoroacetate method. Biological effects caused by the introduction of the fluorine atom in these products were discussed based on the chemical character of fluorine.