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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/25000

    Title: Highly stereoselective and stereospecific syntheses of a variety of quercitols from d-(−)-quinic acid
    Authors: 施增廉;Shih, Tzenge-lien;Lin, Ya-Ling;Kuo, Wei-Shen
    Contributors: 淡江大學化學學系
    Keywords: Quercitol;d-(−)-Quinic acid;Dihydroxylation;Glycosidase
    Date: 2005-02-14
    Issue Date: 2009-12-01
    Publisher: Kidlington: Pergamon
    Abstract: The highly stereoselective synthesis of (−)-epi-, (−)-allo- and neo-quercitols as well as stereospecific synthesis of (−)-talo- and (+)-gala-quercitols have been achieved. The general strategy is employing dihydroxylation of the isolated double bond of various kinds of protected chiral (1,4,5)-cyclohex-2-ene-triols, which are derived from d-(−)-quinic acid. The choosing of protecting groups from either BBA (butane 2,3-bisacetal) or acetyl groups will result in the various degrees of stereoselectivity of dihydroxylation. On the other hand, the cyclohexylidene acetal moiety is attributed to the stereospecificity during dihydroxylation to afford the request molecules.
    Relation: Tetrahedron 61(7), pp.1919-1924
    DOI: 10.1016/j.tet.2004.11.084
    Appears in Collections:[Graduate Institute & Department of Chemistry] Journal Article

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