The synthesis and resolution of (±)-1,5,6-tri- O-benzyl- myo-inositol

Racemic 1,5,6-tri- O-benzyl- myo-inositol was prepared by five routes and converted into 1,5,6-tri- O-benzyl-2,3- O-isopropylidene- myo-inositol, the camphanates of which were readily separated by chromatography. The absolute configurations of the chiral derivatives were established by their conversion into the known chiral 1,4,5,6-tetra- O-benzyl- myo-inositols. 1 d-1,5,6-Tri- O-benzyl-2,3- O-isopropylidene- myo-inositol was converted into 1 d-1,3,5,6-tetra- O-benzyl- myo-inositol and thence into 1 d-2,4-di- O-methyl- myo-inositol. 1 d-1,5,6-Tri- O-benzyl- myo-inositol was converted into 1 d-1,2,5,6-tetra- O-benzyl- myo-inositol, the diacetate of which is a chiral analogue of “thermosalient crystals”. The potential of the above compounds for the synthesis of natural products is surveyed.