6383-00-2Relevant academic research and scientific papers
The orientation of the β-hydroxyl group controls the diastereoselectivity during the hydride reduction and Grignard reaction of inososes
Jagdhane, Rajendra C.,Patil, Madhuri T.,Krishnaswamy, Shobhana,Shashidhar, Mysore S.
, p. 5144 - 5151 (2013/06/27)
A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the β-hydroxyl group (or i
Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
Devaraj, Subramanian,Jagdhane, Rajendra C.,Shashidhar, Mysore S.
experimental part, p. 1159 - 1166 (2009/10/04)
O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.
