Cyclitols. XXIX. Polyphosphorylation of polyols. The synthesis of myo-inositol pentaphosphates

Abstract

Heating myo-inositol with an excess of the triethylammonium salt of N- benzoylphosphoramidic acid in N,N-dimethylformamide results in phosphorylation of every hydroxyl group. The method appears to be general for the complete phosphorylation of unsubstituted or partially substituted inositols. Starting with 1-O-benzyl- and 4-O-benzyl-myo- inositol, phosphorylation and subsequent hydrogenolysis gave DL-myo- inositol 1,2,4,5,6- and 1,2,3,4,5-pentaphosphate, respectively. Other methods of phosphorylation were found unsuitable.