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研究生： 林育聖
Yu-Sheng Lin
論文名稱： 一、應用路易士酸催化斷裂carbamate與carbonate樹脂
1. Lewis acid-catalyzed cleavage of carbamate and carbonate resin; 2. Development of novel oxidatively removable and recyclable linkers for combinatorial solid phase synthesis
指導教授： 李文仁
Wen-Ren Li
口試委員:
學位類別： 碩士
Master
系所名稱： 理學院 - 化學學系
Department of Chemistry
畢業學年度： 89
語文別： 中文
論文頁數： 181
中文關鍵詞： 組合式化學 、相合成 、鍵鏈劑
外文關鍵詞： combinatiorial chemistry, olid phase synthesis
相關次數： 點閱：8  下載：0 
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    • 在與Merrifield樹脂鍵鏈的benzyloxycarbonyl當量上製備醯胺與酯類的程序已經被發展了。聚合物支撐的carbamates與溴化鋅及適當的鹵化醯基在三乙基胺的存在下反應得很乾淨產生他們相對的醯胺且具高產率與高純度。與樹脂鍵鏈的carbonates的斷裂也適用類似的系統去斷裂產生乙酸酯或苯甲酸酯，但並不需要三乙胺的參與。
    第二章
    兩種新穎、可重複使用且用氧化劑CAN斷裂的phenanthridine鍵鏈劑在此被介紹。這些鍵鏈劑基於雙取代醯胺被設計為?酸基化合物的氧化斷裂，但是卻能容忍酸、鹼與還原的反應條件。這些鍵鏈劑在固相有機合成上的應用產生具高產率與高純度的產物。


    A procedure for the preparation of amides and esters on a Merrifield resin- bound benzyloxycarbonyl equivalent has been developed. Ploymer- supported carbamates react cleanly with zinc bromide and the appropriate acyl halide in the presence of triethylamine to provide their corresponding amides in high yields and purities. Cleavage of resin-bound carbonates was carried out using the similar reagent systems in the absence of triethylamine to give acetate and benzoates.
    Chapter II
    Two novel, reusable phenanthridine linkers that use ceric ammonium nitrate (CAN) as a cleavage reagent are described. These linkers are based on a disubstituted amide and are designed for the release of carboxylic acids, but tolerate exposure to acidic, basic, and reductive reactions. Application of these linkers to solid phase organic synthesis affords products in excellent yields and high purities.

    謝誌 I 中文摘要 II Abstracts III 目錄 IV 圖目錄 VI 表目錄 VIII 第一章 應用路易士酸催化斷裂carbamate與carbonate樹脂 1 1-1導論 2 1-2結果與討論 11 1-2-1. 應用路易士酸催化斷裂carbamate與carbonate樹脂 11 1-2-2. 結論 14 1-3 實驗流程及光譜數據 15 1-3-1 實驗儀器: 15 1-3-2 實驗藥品 16 1-3-3 一般的實驗方法 17 1-3-6 Resin-bound carbamate斷裂的流程 19 1-3-7 Resin-bound carbonate 斷裂的流程 26 第二章 研發新型氧化斷裂且可重複利用的鍵鏈劑 29 2-1導論 30 2-2-1 鍵鏈劑的簡介 30 2-1-2 Phenanthridine鍵鏈劑的設計原由 33 2-2結果與討論 35 2-2-1 鍵鏈劑18的合成 35 2-2-3 鍵鏈劑19的合成步驟 38 2-2-4 Phenanthridine鍵鏈劑於固相合成的應用 39 2-2-5 三種鍵鏈劑的比較 44 2-2-6 結論 46 2-3 實驗流程及光譜數據 47 2-3-1 實驗儀器: 47 1-3-2 實驗藥品 48 2-3-3 一般的實驗方法 49 2-3-4 2-Phenanthridine-2-yl-ethanol鍵鏈劑的合成 50 2-3-5 鍵鏈劑19的合成方法 58 2-3-6 應用鍵鏈劑17、18、19於固相合成2-[4-(acetyl-methyl- amino)-phenyl]-2-methyl- propionic acid 36的實驗步驟 60 2-3-7 固相合成Bz-L-Phe-L-Ala-OH 42 64 參考文獻 70 附錄 73

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