Synthesis of [(2S,3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic Acid Derivatives: New Leads as Selective β-Galactosidase Inhibitors

The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from -glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 glycosidases. Ester (6) is a selective inhibitor of β-galactosidases. The new compounds represent a new type of imino-C-nucleoside analogues.