A convenient synthesis of d-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and l-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3)

An efficient synthesis of an optically active inositol derivative that is a precursor to d-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (−)) is described. Crystallization of the diastereomers of (±)-1-O-[(+)-menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (−)-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (±)-3-O-[(−)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to d-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3, (+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as d-myo-inositol 1,3,4,5-tetrakisphosphate.