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. 1D-1,5,6-Tri-O-benzyl-2,3-O-isopropylidene-myo-inositol was converted into 1D-1,3,5,6-tetra-O-benzyl-myo-inositol and thence into 1D-2,4-di-O-methyl-myo-inositol. 1D-1,5,6-Tri-O-benzyl-myo-inositol was converted into 1D-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.

Citation

T Desai, A Fernandez-Mayoralas, J Gigg, R Gigg, S Payne. The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol. Carbohydrate research. 1990 Sep 19;205:105-23

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PMID: 2276129

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