Regioselective protection of myo-inositol orthoesters – recent developments

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Regioselective Opening of myo-Inositol Orthoesters: Mechanism and Synthetic Utility

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-pentakisphosp...

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Metal trifluoromethanesulfonate-catalyzed regioselective acylation of myo-inositol 1,3,5-orthoformate.

A highly regioselective acylation of myo-inositol 1,3,5-orthoformate at the 4-O/6-O positions is catalyzed by various metal trifluoromethanesulfonates, giving excellent yields; an asymmetric example using (-)-camphanic anhydride is described here.

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ژورنال

عنوان ژورنال: Arkivoc

سال: 2002

ISSN: 1551-7012

DOI: 10.3998/ark.5550190.0003.708