An Efficient Synthesis of the Glycosidase Inhibitor 1,6-Dideoxy-6,6- difluoronojirimycin

Abstract

1,6-Dideoxy-6,6-difluoronojirimycin (1) was prepared from an easily accessible and commercially available starting material, methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside. Key steps of this synthesis are a difluorination reaction using DAST and a reductive amination. The overall yield of the synthesis is 44%. Compound 1 has been tested for its activity as an inhibitor of various glucosidases and galactosidases. © 2011 Verlag der Zeitschrift für Naturforschung, Tübingen.