Vibhute, Amol M.; Sureshan, Kana M. published an article in 2013, the title of the article was H2SO4-silica: an eco-friendly heterogeneous catalyst for the differential protection of myo-inositol hydroxyl groups.Computed Properties of 707-07-3 And the article contains the following content:
There is enormous interest in myo-inositol derivatives as they serve as precursors for the synthesis of several biol. important phosphoinositols, natural products, catalyst, supramol. architectures etc. However the presence of six secondary hydroxy groups of similar reactivity warrants protection of inositol hydroxyl groups for effective synthesis. Acid catalyzed protection of inositol hydroxyl groups as ortho esters or ketals are the most commonly used protecting strategy in inositol chem. Traditionally, homogeneous acid catalysts such as para-toluenesulfonic acid (p-TSA) or camphorsulfonic acid (CSA) are used for these transformations. While the reversible nature of these reactions necessitates the catalyst removal, aqueous work up cannot be employed for their removal as the products are water soluble The authors have circumvented this problem by using H2SO4-silica as the solid supported catalyst, which can be removed by filtration, for these transformations. Treatment of myoinositol with trialkyl ortho esters in presence of H2SO4-silica under normal conditions resulted in esterification at the least reactive hydroxyl group (C2-OH) giving exclusively the corresponding 2-O-acyl-myo-inositol. By doing the reaction in a rotary evaporator under reduced pressure resulted in the formation of the corresponding ortho esters, wherein three hydroxyl groups of inositol are protected simultaneously. The authors could synthesize different myo-inositol ortho esters 6-10 in excellent yields by this method. Ketalization of myo-inositol with one equivalent of 1,1-dimethoxycyclohexane or 2,2-dimethoxypropane in presence of H2SO4-silica under similar conditions resulted in the simultaneous protection of 1-OH and 2-OH giving the 1,2-O-cyclohexylidene-myo-inositol or 1,2-O-isopropylidene-myo-inositol in excellent yields. Also, diketalization of myo-inositol with 2,2-dimethoxypropane gave three diketals namely (±)-1,2:4,5-di-O-isopropylidene-myo-inositol (±)-1,2:5,6-di-O-isopropylidene-myo-inositol and (±)-1,2:3,4-di-O-isopropylidene-myoinositol in considerable yields. Similarly when dimethoxycyclohexane was used, the dicyclohexylidene derivatives (±)-1,2:4,5-di-O-cyclohexylidene-myo-inositol (±)-1,2:5,6-di-O-cyclohexylidene-myo-inositol and (±)-1,2:3,4-di-O-cyclohexylidene-myo-inositol were obtained in good yield. While the yields of 1,2:3,4-di-O-alkylidene-myo-inositols are negligibly small by other known methods, interestingly, our method give these diketals in good yields and hence can be exploited synthetically. Thus by using a cheap, eco-friendly, easy-to-make and easy-to-handle H2SO4-silica as the catalyst (green chem. method) the authors could tune the conditions to make mono-protected, di-protected, tri-protected or tetra-protected inositol derivatives This strategy can be applied for the economic synthesis of various key intermediates of inositol for various purposes. The title compounds thus formed included a myo-inositol ketal (I) and related substances. The synthesis of the target compounds was achieved using ortho esters, such as (trimethoxymethyl)benzene, 1,1,1-triethoxypentane, 1,1,1-triethoxybutane, 1,1-dimethoxycyclohexane, etc. as starting materials. The experimental process involved the reaction of (Trimethoxymethyl)benzene(cas: 707-07-3).Computed Properties of 707-07-3
The Article related to inositol ortho ester preparation protective group, ketal inositol preparation protective group green chem solid acid, Carbohydrates: Alditols, Cyclitols, Glycerides and other aspects.Computed Properties of 707-07-3
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