Regioselective phosphorylation of vicinal 3,4-hydroxy myo-inositol derivative promoted practical synthesis of d-PtdIns(4,5)P2 and d-Ins(1,4,5)P3

The reactivity of 3 and 4-OH in 3,4-diol myo-inositol derivatives were observed through the phosphorylation, acylation and silylation. The results indicated that 3-OH is much more reactive than 4-OH, giving regiospecifically 3-mono-functionalized products. This investigation provided a concise methodology for the synthesis of natural d-form of PtdIns(4,5)P2 and d-Ins(1,4,5)P3 from l-1,2-O-cyclohexylidene-3,4-O-(tetraisopropyl disiloxane-1,3-diyl)-myo-inositol.