Solid and solution state conformations of (±)-3-O-acetyl-1,2:4,5-di-O-isopropylidene-allo-inositol and (±)-3-O-acetyl-1,2:4,5-di-O-isopropylidene-6-O-methyl-allo-inositol

Abstract

The synthesis and conformational studies of (±)-3-O-acetyl-1,2:4,5-di-O-isopropylidene-allo-inositol and (±)-3-O-acetyl-1,2:4,5-di-O-isopropylidene-6-O-methyl-allo-inositol are described. Solid state conformations of the title compounds have been studied by solving their X-ray crystal structures. The inositol ring in both the compounds deviate considerably from the ideal chair conformation to flattened chair conformation in the solid state. Their conformations in solution were studied by the use of 1H NMR spectroscopy. These conformational analyses revealed that the title compounds adopt similar conformations in solid and solution states irrespective of the solvent polarity.