標題: 以砜基為連結元件的固相有機合成及化合物庫之合成研究
Studies of the Sulfone Linker in Solid-Phase Organic Synthesis and Compound Library
作者: 陳志豪
鍾文聖
吳獻仁
Wen-Sheng Chung
Hsien-Jen Wu
應用化學系碩博士班
關鍵字: 固相有機合成;Solid phase organic synthesis
公開日期: 2003
摘要: 摘要 在本論文中,我們以砜基樹酯為固相有機合成之載體,並開發三甲基鋁為產物之切割試劑,成功的合成出結構骨架類似化合物Ⅰ及化合物Ⅱ之小型化合物庫。 首先,在液相反應中我們以benzene sulfinic acid sodium salt為起始物,經歷六個反應步驟,得到化合物7,總產率約為15 %,並確認合成結構骨架類似化合物Ⅰ及化合物Ⅱ之反應流程的可行性。 接著,我們在實驗室成功的製備以砜基為連結元件之樹酯8;應用此砜基樹酯8為固相有機合成之載體,經由類似液相反應所建立之合成反應條件。最後,並以三甲基鋁為切割試劑,順利將產物由固相載體中釋放出來;應用此固相有機合成技術,我們成功的合成了化合物16、18、21、26、28、31、33、38、41、46及48等11個具有類似結構骨架之化合物庫。 未來希望在國內學術界找到合適的合作對象,測試這些化合物是否具有藥物活性。 化合物I 化合物Ⅱ
Abstract Using sulfinate functionalized resin as a solid support, we have developed a new cleavage reagent, Al(CH3)3, and successfully synthesized a small library of compounds with structures like compound Ⅰ and Ⅱ. First of all, benzene sulfinic acid sodium salt was used as starting material in liquid phase experiment. Through six reaction steps, we obtained compound 7 in about 15% total yield, which demonstrated that compounds similar to Ⅰ and Ⅱ can be synthesized. Then, we successfully prepared resin 8 which has sulfone linker. Using resin 8 as solid support in SPOS, similar reaction conditions in liquid phase and Al(CH3)3 as cleavage reagent, we obtained the products form solid support. Application of SPOS technique, we synthesized a library of compounds which includes 16, 18, 21, 26, 28, 31, 33, 38, 41, 46 and 48. In the future, we hope to search a cooperative group in the academia to test the potential bioactivity of these compounds. Compound I Compound Ⅱ
URI: http://140.113.39.130/cdrfb3/record/nctu/#GT009125507
http://hdl.handle.net/11536/54680
Appears in Collections:Thesis


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