01863nas a2200229   4500008004100000022001400041245009600055210006900151260009900220300001400319490000800333520101200341653001701353653001401370653001301384653001301397653002101410100002501431700002701456700002701483856012301510       2009                        eng d  a0008-621500aRelative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation0 aRelative reactivity of hydroxyl groups in inositol derivatives r  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLANDbELSEVIER SCI LTDcJUL  a1159-11660 v3443 a<p>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. (C) 2009 Elsevier Ltd. All rights reserved.</p>10aCarbohydrate10aChelation10aCyclitol10aInositol10aProtecting group1 aDevaraj, Subramanian1 aJagdhane, Rajendra, C.1 aShashidhar, Mysore, S.  uhttps://library.ncl.res.in/content/relative-reactivity-hydroxyl-groups-inositol-derivatives-role-metal-ion-chelation-0