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

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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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Interaction of myo-inositol hexakisphosphate with biogenic and synthetic polyamines.

Within all the eukaryotic cells myo-inositol phosphates (InsPs) are an important group of biomolecules that are potentially related to signaling functions. The most abundant member of this family in nature is InsP6 (phytate, L(12-) in its fully deprotonated form). The complicated chemical behavior of this molecule demands a great effort to understand its function in the cell medium. In this wor...

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Full title : The utility of urinary myo - inositol as

192 words) Objective: The most common screening tests for glucose intolerance are fasting plasma glucose (FPG) and glycated hemoglobin (HbA1c). Because it reflects the current status of hyperglycemia, urinary myo-inositol (UMI) may be useful. We evaluated UMI as a screening tool for glucose intolerance. Design and Methods: A cross-sectional, community-based population study of 1057 Japanese res...

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ژورنال

عنوان ژورنال: The Journal of Organic Chemistry

سال: 2013

ISSN: 0022-3263,1520-6904

DOI: 10.1021/jo3027774