Activation of certain pharmaceutical drugs requires a phosphorylation reaction to take place, where an alcohol group is converted to a phosphate. One such example is the diol FTY720, a drug used in the  treatment of multiple sclerosis. When ingested, FTY720 is phosphorylated selectively by <i>sphingosine kinase</i> - where only one of the two alcohols is converted to a phosphate - generating the active drug (S)-FTY720-phosphate. We have previously published on the Lewis acid catalyzed phosphorylation of diols with pyrophosphate reagents. Our poster presents three areas of current study on developing an enantioselective phosphorylation of diols. First, different diols were screened in order to investigate what structural features are necessary for selectivity. Second, catalyst loading was examined. Third, experiments to elucidate the absolute configuration of the product are discussed. We hope to continue improving the enantioselectivity of the phosphorylation and use this knowledge to complete a selective laboratory phosphorylation of FTY720.<br/>

Enantioselective phosphorylation of diols

2019 Spring National Meeting

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