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- W2952675406 abstract "Abstract Hydration of methyl diepoxystearate ( 2 ) at high cytosolic epoxide hydrolase (CEH) concentration produces the corresponding tetraol, while at physiological CEH concentration four tetrahydrofuran diol products ( 3–6 ) are produced. These same four products are obtained in the acid-catalyzed hydration of 2 . Spectroscopic studies, primarily EI mass spectrometry and difference spectrum NOE, are reported which establish the regio- and stereoselectivity of 2 → 3–6 (MS differentiating 3 4 from 5 6 and NOE differentiating 3 5 from 4 6 ). The observed syn arrangement of the two adjacent groups (i.e., substituents at C 2 and C 3 ) in the four THF-diols can only arise from an A 2 type opening of the first epoxide. The resulting epoxydiol intermediate then cyclizes by A 2 opening of the second cis -epoxide as established by synthesis of these hypothetical epoxydiol intermediates and their subsequent conversion to THF-diols 3–6 ." @default.
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- W2952675406 date "2010-08-20" @default.
- W2952675406 modified "2023-09-25" @default.
- W2952675406 title "ChemInform Abstract: Stereochemical Aspects of Cytosolic Epoxide Hydrolase Hydration of Methyl Diepoxystearates." @default.
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- W2952675406 doi "https://doi.org/10.1002/chin.199329058" @default.
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