Synthesis and evaluation of 1,5,6-trideoxy-6,6-difluoro-1,5-imino-d-glucitol (1,6-dideoxy-6,6-difluoronojirimycin) as a glucosidase inhibitor

1,5,6-Trideoxy-6,6-difluoro-1,5-imino-d-glucitol hydrochloride (2) and 1,5,6-trideoxy-6,6-difluoro-1,5-imino-d-glucitol (3) have been synthesized from l-sorbose. The formation of the C-5 difluoromethyl group was accomplished by difluorination of a carbonyl group by DAST. The results of in vitro enzymic evaluation of 3 indicate that it is a competitive inhibitor of yeast α-glucosidase (Ki = 7.5 mM) and a noncompetitive inhibitor of almond β-glucosidase (Ki = 8.7 m).