Chemistry Letters, Vol.32, No.8, 724-725, 2003
Enantiomerically convergent synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate from both L- and D-1,2-0-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.