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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/61579

    Title: Efficient syntheses of (−)-shikimate and (−)-quinate 3-phosphate via trans vicinal diol protection with 2,2,3,3-tetramethoxybutane (TMB) of shikimic and quinic acids
    Authors: Shih, Tzenge-lien;Wu, S. H.
    Contributors: 淡江大學化學學系
    Keywords: shikimic acid;quinic acid;shikimate 3-phosphate;quinate 3-phosphate;2,2,3,3-tetramethoxybutane
    Date: 2000-04-01
    Issue Date: 2011-10-15 23:18:37 (UTC+8)
    Abstract: (−)-Shikimate 3-phosphate and (−)-quinate 3-phosphate can be synthesized by selective protection of their trans diol functionality using 2,2,3,3-tetramethoxybutane (TMB) using d-(−)-shikimic acid and d-(−)-quinic acid as starting materials. This versatile reagent facilitates the synthesis of these important biological targets in fewer steps than previously reported. By the proper choice of protecting group for C-3 hydroxyl in d-(−)-quinic acid, it can be converted to a key intermediate in the synthesis of (−)-shikimate 3-phosphate.
    Relation: Tetrahedron letters41, pp.2957-2959
    DOI: 10.1016/S0040-4039(00)00280-X
    Appears in Collections:[Graduate Institute & Department of Chemistry] Journal Article

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