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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/24973

    Title: Expeditious Synthesis of New 3,4,6-Trihydroxythiepanes from d-(-)-Quinic Acid
    Authors: Shih, Tzenge-lien;Fang, Yi-chuan
    Contributors: 淡江大學化學學系
    Keywords: quinic acid;thiepane;thiosugar
    Date: 2007-01
    Issue Date: 2010-08-10 09:54:06 (UTC+8)
    Publisher: Philadelphia: Taylor & Francis Inc.
    Abstract: We report herein that the new seven-membered-ring thiosugars (thiepanes) have been synthesized from d-(-)-quinic acid. The key feature of the synthesis involves the thiocyclization of protected hexane-1,2,3,5,6-pentanol derivatives. The subsequent step of acidic removal of protecting groups is critical in the reaction conditions to obtain the required 3,4,6-trihydroxythiepanes. During the course of studies, the unexpected trihydroxythiopyrans are formed because of the ring contractions of their corresponding trihydroxythiepanes under various conditions.
    Relation: Synthetic Communications 37(19), pp.3337-3349
    DOI: 10.1080/00397910701490113
    Appears in Collections:[Graduate Institute & Department of Chemistry] Journal Article

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