Regioselective opening of myo-inositol orthoesters: Mechanism and synthetic utility

Himali Y. Godage, Andrew M. Riley, Tim J. Woodman, Mark P. Thomas, Mary F. Mahon, Barry V. L. Potter

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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)CD 2R), 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.
Original languageEnglish
Pages (from-to)2275-2288
JournalJournal of Organic Chemistry
Volume78
Issue number6
Early online date25 Feb 2013
DOIs
Publication statusPublished - 15 Mar 2013

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