A Novel Regioselective Desulfation Method Specific to Silyl Ester of Primary Sulfate Using Silylating Agents. Selective Preparation of Secondary Alkyl Sulfates Having a Primary Hydroxy Group

The treatment of bis(trimethylsilyl)ester of 1-O-decylglycerol-2,3-disulfate with trimethylsilyl-N-trimethylsilylacetimidate (BSA) or (dimethylamino)trimethylsilane caused regioselective desulfation to afford 1-O-decyl glycerol-2-sulfate selectively in good yield. Silylating agents, having nitrogen, seems to be responsible for facilitating trimethylsiloxysulfonyl cation transfer.