Synthesis and oxidation of thioglicosides underlain by neomenthanethiol, D-glucose, and D-fructose.

Synthesis of sulfides proceeding from neomenthanethiol, 1,2- O-isopropylidene-α- D-glucofuranose and 2,3:4,5-di- O-isopropylidene-β- D-fructopyranose was performed to get 65 and 54% yield respectively. Oxidation of the sulfides afforded diastereomeric sulfoxides in the yields from 40 to 53%, and diastereomeric excess (de) up to 36%. After removing the isopropylidene protection from 1-deoxy-1-[(1 S,2 S,5 R)-2-isopropyl-5-methylcyclohexylsulfanyl]-2,3:4,5-di- O-isopropylidene-β- D-fructopyranose a water-soluble sulfide was obtained. [ABSTRACT FROM AUTHOR]