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    Please use this identifier to cite or link to this item: http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/32764

    Title: 合成L-sugar的新方法及利用D-(-)-quinic acid經Beckmann rearrangement合成trihydroxyazepanes
    Other Titles: A new synthesis of l-sugar and the use of D-(-)-quinic acid for synthesis of trihydroxyazepanes via beckmann rearrangement
    Authors: 曾瑞晃;Tseng, Jui-huang
    Contributors: 淡江大學化學學系碩士班
    施增廉;Shih, Tzenge-lien
    Keywords: L-醣類;重排反應;L-sugar;azepanes;Beckmann rearrangement
    Date: 2005
    Issue Date: 2010-01-11 02:43:00 (UTC+8)
    Abstract: 近年來,由於L-carbohydrate在醫學界的應用,引起了許多的注意,故有許多文獻報導。
    由D-(-)-quinic acid為起始物,利用Beckmann rearrangement反應得到具保護基之七圓環azasugar,進一步在去除保護基即可獲得trihydroxyazepane。
    Recently, L-carbohydrate have been widely used in drug development. We reported herein an efficient synthesis of L-allono-1,4-lactone from D-mannono-1,4
    -lactone in five-step sequence. The key feature of the method involved a one pot "double inversion” procedure at stereocenter of C-4 and C-5 of D-mannono-1,4
    -lactone to obtain the L-allono-1,4-lactone.
    On the other hand, azasugars played an important role as glycosidase inhibitors. They were used in treatment of cancer, viral infection and diabetes, and have potential to make new drugs.
    There are many reports to azasugars which they focused much attentation on the preparation of various five- and six-member azasugars namely polyhydroxy pyrrolidine and piperidine, respectively. However, only a few reports have appeared to the synthesis of seven-member azasugar-azepanes. Tetrahydroxy-azepanes appeared most in literatures among seven-member azasugars. Only few cases of trihydroxyazepanes and dihydroxyazepanes were described. Two trihydroxyazepanes were synthesized via Beckmann rearrangement from readily available D-(-)-quinic acid and reported in this article.
    Appears in Collections:[化學學系暨研究所] 學位論文

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