Comparison of racemic epi-inosose and (−)-epi-inosose

• Published in: Acta crystallographica. Section C, Crystal structure communications Vol. 67; no. 11; pp. o435 - o438
• Main Authors: Krishnaswamy, Shobhana, Patil, Madhuri T., Shashidhar, Mysore S.
• Format: Journal Article
• Language: English
• Published: 5 Abbey Square, Chester, Cheshire CH1 2HU, England International Union of Crystallography 01.11.2011; Wiley Subscription Services, Inc
• Subjects: Asymmetry; Atoms & subatomic particles; Conversion; Crystal structure; Crystallization; Crystallography; Crystallography, X-Ray; Crystals; Hydrogen Bonding; Hydrogen bonds; Inositol - analogs & derivatives; Inositol - chemistry; Lattices; Molecular Conformation; Molecular Structure; Molecules; Optical activity
• ISSN: 0108-2701; 1600-5759
• DOI: 10.1107/S0108270111039412

The conversion of myo‐inositol to epi‐inositol can be achieved by the hydride reduction of an intermediate epi‐inosose derived from myo‐inositol. (−)‐epi‐Inosose, (I), crystallized in the monoclinic space group P21, with two independent molecules in the asymmetric unit [Hosomi et al. (2000). Acta Cryst. C56, e584–e585]. On the other hand, (2RS,3SR,5SR,6SR)‐epi‐inosose, C6H10O6, (II), crystallized in the orthorhombic space group Pca21. Interestingly, the conformation of the molecules in the two structures is nearly the same, the only difference being the orientation of the C‐3 and C‐4 hydroxy H atoms. As a result, the molecular organization achieved mainly through strong O—H...O hydrogen bonding in the racemic and homochiral lattices is similar. The compound also follows Wallach's rule, in that the racemic crystals are denser than the optically active form.