Protecting group directed stereoselective reduction of an epi-inosose: efficient synthesis of epi-inositol

Patil, Madhuri T.; Sarmah, Manash P.; Shashidhar, Mysore S.

doi:10.1016/j.tetlet.2011.05.051

Cited by 3 publications

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“…Racemic epi-inosose, (II), was synthesized as reported previously (Patil et al, 2011). Prism-shaped crystals (m.p.…”

Section: Methodsmentioning

confidence: 99%

“…epi-Inositol is known to affect regulation of the myo-inositol biosynthetic pathway (Shaldubina et al, 2002) and has been evaluated as a potential antidepressant drug that could interact with the Li + ion and myo-inositol receptors in the brain (Einat et al, 1998;Belmaker et al, 1998;Williams et al, 2002). We have reported previously the synthesis of epiinositol by the reduction of racemic epi-inosose (Patil et al, 2011).…”

Section: Commentmentioning

confidence: 99%

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

Patil

Shashidhar

2011

Acta Crystallogr C

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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.

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“…Racemic epi-inosose, (II), was synthesized as reported previously (Patil et al, 2011). Prism-shaped crystals (m.p.…”

Section: Methodsmentioning

confidence: 99%