Synthesis of thiosugars as weak inhibitors of glycosidases

Article abstract of DOI:10.1016/S0040-4020(97)10096-5

A series of enantiomerically pure thiosugars (1,6-dideoxy-1,6-thio-D- mannitol or L-iditol, 1,5-dideoxy-1,5-thio-L-gulitol or D-glucitol and 2,5- dideoxy-2,5-thio-L-iditol or D-mannitol, and their corresponding sulfoxide or sulfone) was synthesized via thiocyclization of C₂-symmetric bis-epoxides, and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (α- and β-D- glucosidases, α-D-mannosidase and α-L-fucosidase).