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• W2012105589 abstract "Acid hydrolysis of myo-inositol 1,3,5-orthoesters, apart from orthoformates, exclusively affords the corresponding 2-O-acyl myo-inositol products via a 1,2-bridged five-membered ring dioxolanylium ion intermediate observed by NMR spectroscopy. These C-2-substituted inositol derivatives provide valuable precursors for rapid and highly efficient routes to 2-O-acyl inositol 1,3,4,5,6-pentakisphosphates and myo-inositol 1,3,4,5,6-pentakisphosphate with biologically interesting and anticancer properties. Deuterium incorporation into the α-methylene group of such alkyl ester products (2-O-C(O)CD2R), when the analogous alkyl orthoester is treated with deuterated acid, is established utilizing the novel orthoester myo-inositol 1,3,5-orthobutyrate as an example. Such deuterated ester products provide intermediates for deuterium-labeled synthetic analogues. Investigation into this selective formation of 2-O-ester products and the deuterium incorporation is presented with proposed mechanisms from NMR experiments." @default.
• W2012105589 created "2016-06-24" @default.
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• W2012105589 date "2013-03-05" @default.
• W2012105589 modified "2023-10-16" @default.
• W2012105589 title "Regioselective Opening of <i>myo</i>-Inositol Orthoesters: Mechanism and Synthetic Utility" @default.
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• W2012105589 doi "https://doi.org/10.1021/jo3027774" @default.
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