Synthesis of some thiosucrose derivatives

Abstract

Treatment of 3,3',4',6'-tetra-O-acetylsucrose in dimethylformamide with thioacetic acid, triphenyl- phosphine and diethyl azodicarboxylate, followed by acetylation, gave 6-thiosucrose octaacetate in good yield. Similar treatment of 4,6:2,1'-di-O-isopropylidenesucrose followed by removal of the isopropylidene groups and acetylation gave 6'-thiosucrose octaacetate. Treatment of sucrose itself under these conditions gave 6,6'-dithiosucrose octaacetate. 6,6'-Dithiosucrose octaacetate was readily converted into 6,6'-dideoxysucrose by treatment with Raney nickel followed by deacetylation.