Abstract
(+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-β-valienamine (NOEV, 3) and N-octyl-β-valienamine (NOV, 4).
Copyright © 2011 Elsevier Ltd. All rights reserved.
MeSH terms
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Aniline Compounds / chemistry
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Animals
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Carbohydrate Sequence
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Cattle
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Cyclohexanes / chemistry*
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Ecdysone / analogs & derivatives
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Ecdysone / chemistry
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Enzyme Inhibitors / chemistry
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Hexosamines / chemistry*
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Inhibitory Concentration 50
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Inositol / analogs & derivatives*
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Inositol / chemical synthesis
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Inositol / chemistry
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Liver / enzymology
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Methylene Chloride / chemistry*
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Molecular Sequence Data
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Structure-Activity Relationship
Substances
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Aniline Compounds
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Cyclohexanes
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Enzyme Inhibitors
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Hexosamines
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N-octyl-beta-valienamine
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proto-quercitol
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vibo-quercitol
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3,5,14-trihydroxycholest-7-en-6-one
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Ecdysone
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Cyclohexane
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Inositol
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Methylene Chloride
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aniline