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- W2023163351 abstract "A new and efficient route to homochiral (+)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol and its 2-benzyl ether derivative is described, starting from (−)-quinic acid. The compounds are key intermediates in the solution-phase and solid-phase synthesis of inhibitors for inositol monophosphatase. The pivotal step involves a La3+-induced reversal of the diastereoselectivity for the borohydride reduction of an intermediate cyclohexan-4-one. (1R,2R,4R,6R)-(O6-Propyl)cyclohexane-1,2,4,6-tetraol 1-phosphate, predicted to be a submicromolar competitive inhibitor of inositol monophosphatase, was prepared from the title epoxide in 5 steps in good overall yield. The compound proved to be a competitive inhibitor and displayed the expected potency confirming the stereochemical requirements for inhibition. The O2-benzylated epoxide derivative could be stereospecifically alcoholysed using either BF3·(OEt)2 or Yb(III)(OTf)3 as catalysts without appreciable levels of benzyl ether protecting group cleavage. The preparation of the alcoholysis products (1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-isopropyloxycyclohexanol and (1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-(phenethyloxy)cyclohexanol, and the synthesis and evaluation of the inhibitor (1R,2R,4R,6R,2′S)-6-(1′-hydroxy-3′-phenylpropan-2-yloxy)-2,4-dihydroxycyclohexyl phosphate and its diastereomer (1R,2R,4R,6R,2′R)-6-(1′-hydroxy-3′-phenylpropan-2-yloxy)-2,4-dihydroxycyclohexyl phosphate are described." @default.
- W2023163351 created "2016-06-24" @default.
- W2023163351 creator A5020699680 @default.
- W2023163351 creator A5073072817 @default.
- W2023163351 date "2010-08-04" @default.
- W2023163351 modified "2023-09-26" @default.
- W2023163351 title "ChemInform Abstract: Synthesis of (-)-(1R,2R,4R,6S)-1,6-Epoxy-4-benzyloxycyclohexan-2-ol, a Key Precursor to Inositol Monophosphatase Inhibitors, from (-)-Quinic Acid." @default.
- W2023163351 cites W2903493684 @default.
- W2023163351 doi "https://doi.org/10.1002/chin.199716229" @default.
- W2023163351 hasPublicationYear "2010" @default.
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