Open AccessComparison of racemic epi ‐inosose and (−)‐ epi ‐inosose
Author(s) -
Krishnaswamy Shobhana,
Patil Madhuri T.,
Shashidhar Mysore S.
Publication year - 2011
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270111039412
Subject(s) - monoclinic crystal system , chemistry , group (periodic table) , hydrogen bond , stereochemistry , crystallography , crystal structure , molecule , organic chemistry
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 P 2 1 , with two independent molecules in the asymmetric unit [Hosomi et al. (2000). Acta Cryst. C 56 , e584–e585]. On the other hand, (2 RS ,3 SR ,5 SR ,6 SR )‐ epi ‐inosose, C 6 H 10 O 6 , (II), crystallized in the orthorhombic space group Pca 2 1 . 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.