Enantiomerically Convergent Synthesis of Phosphatidyl-D-myo-inositol 3,5-Bisphosphate from Both L- and D-1,2-O-Cyclohexylidene-myo-inositol

The synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate [PtdIns(3,5)P2] has been conveniently accomplished via convergent routes starting from both enantiomers, 1,2-O-cyclohexylidene-myo-inositol. The synthetic strategy involves completely regioselective phosphorylation of 3,4-diol and 2,3,6-triol of the suitably protected inositols with the corresponding phosphite in the presence of pyridinium tribromide and 2,6-lutidine, resulting in the formation of 3-O-phosphorylated products, respectively.