Chemistry Letters, Vol.31, No.3, 292-293, 2002
Comparison of cyclic and acyclic phosphites by selective phosphorylation. Synthesis of phosphatidylinositol 4-phosphate
To compare the synthetic utility of cyclic xylylene N,N-diethylphosphoramidite and its acyclic analog, dibenzyl ester, both phosphites derived from them with dipalmitoylglycerol were subjected to the selective phosphorylation at the OH-3 position in 1,2:4,5-di-O-cyclohexylidene-myo-inositol in the presence of pyridinium tribromide, and the cyclic version showed to be much superior to the acyclic. The 3-O-phosphorylated product was conveniently converted into phosphatidylinositol 4-phosphate.