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

Carbohydr Res. 1990 Sep 19:205:105-23. doi: 10.1016/0008-6215(90)80132-m.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzyl Compounds / chemical synthesis*
  • Benzyl Compounds / chemistry
  • Benzyl Compounds / isolation & purification
  • Inositol / analogs & derivatives*
  • Inositol / chemical synthesis
  • Inositol / chemistry
  • Inositol / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Benzyl Compounds
  • 1,5,6-tri-O-benzylmyoinositol
  • Inositol