Synthesis of 1'-Deoxy-1'-fluorosucrose via Sucrose Synthetase Mediated Coupling of 1-Deoxy-1-fluorofructose with Uridine Diphosphate Glucose
1'-Deoxy-1'-fluorosucrose (1) has been synthesized by a sucrose synthetase mediated coupling of 1-deoxy-1-fluoro-D-fructose with UDP-glucose. 1-Deoxy-1-fluoro-D-fructose (2) was prepared from 2,3:4,5-di-O-isopropylidene-D-fructopyranose via tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) reaction upon the corresponding trifylate followed by hydrolysis.Fluorosucrose 1 is stable to hydrolysis by invertase and is recognized by the sucrose carrier protein.