Crystal structure, solid state and solution conformation of 1d-1,4-di-O-[(S)-O-acetylmandeloyl]-2,3:5,6-di-O-isopropylidene-myo-inositol

The X-ray crystal structure of 1d-1,4-di-O-(S)-O-acetylmandeloyl]-2,3:5,6-di-O-isopropylidene-myo-inositol is described. Both inositol ring and OAM (O-acetylmandeloyl) moiety deviate from their respective ideal conformations. Inositol ring adopts a flattened chair conformation while OAM adopts an ap (antiperiplanar) conformation. A comparison of its conformation in solution with that in solid was made by the use of NOESY and anisotropic shielding effect in (1)H NMR. This conformational study revealed that the title compound adopts similar conformations in both the states.