Synthesis of myo-Inositol-1,4,5-2,4,6-and 1,3,5-trisphosphate

Abstract

myo-Inosiol-1,4,5-trisphosphate(1) is well established as a second messenger mobilizing Ca2+ in the intracellular signal transduction pathway. Compound 1 and its positional isomers, myo-Inositol 2,4,6-trisphosphate(2) and -1,3,5-trisphosphate(3) were synthesized from myo-inositol. An efficient synthetic pathway of 1 using myo-inositol-1,2,4-trisbenzoate(6) as the key intermediate, prepared from myo-inositol-1,4-bisbenzoate(5) by regioselective benzoylation at the axial 2-OH over the eqiuatorial 3-OH, is described. Syntheses of 2 and 3 utilizing the monoorthoformate derivative(8) of myo-inositol as the key intermediate are also reported.