Enzymatic racemic resolution of a fluorinated substrate and syntheses of E and Z alkenes as precursors for some biologically active fluorohexoses

Abstract

A fluorinated substrate 6 was prepared and then the enantiomers (6a and 7a) were separated by an enzyme in presence of an acetylating agent. The optical purity of 6a and 7a were determined by derivatising them into their MTPA-esters and then by taking their 19F NMR spectra. It was observed that, PL 266 (enzyme), benzene (solvent), 24 h (time), 40 °C (temp.) and vinyl acetate (acetylating agent) were the ideal conditions for racemic resolution. The optical purity was further improved by changing the solvent (hexane), amount of enzyme (PL 266; 3000 units), reaction time (12 h) and amount of acetylating agent (vinyl acetate; two molar). The optically pure species was used for the preparation of E and Z alkenes. Show more