臺灣博碩士論文加值系統

我們成功利用D-ribose作為起始原料，合成一系列的aza-C-glycoside衍生物、氮原子上烷基取代aza-C-glycoside和雙醣氮醣化合物。我們是利用一個簡單的耦合反應將烷鏈的胺類與ribose醣上五號位置為OMs取代基，在鹼性條件下經歷分子內麥可加成反應即可成功合成出來。
除此之外，我們也利用合成過程中所得到的產物38作為起始物，以乙醚當作架橋合成出雙環氮醣58和氮原子有不同取代基的雙環氮醣60。我們進一步地將合成出來的化合物去保護，希望它們能提供大多數1-deoxynojirimycin衍生物進入，然後成功的被發展為醣苷水解酵素抑制劑。

We successfully synthesized a series of aza-C-glycoside derivatives, N-alkylated aza-C-glycosides and aza-C-disaccharides starting from the commercial D-ribose. Our strategy takes advantage of a direct coupling reaction of alkylated amine with 5-OMs-ribose and further underwent intramolecular hetero-Michael reaction under base condition.
In addition, we also prepared a series of ether bridge bicyclo azasugar 58 and N-alkyl ether bridge bicyclo azasugar derivatives 60 starting from 38. When further deprotected, they may therefore provide access to a large number of variously substituted analogues of 1-deoxynojirimycin which are useful for the development of potent glycosidase inhibitors.

簡寫表
中文摘要
英文摘要
第一章 緒論………………………………………1
1.1 研究動機……………………………………1
1.2 醣苷水解酵素抑制劑……………………………2
1.3 醣苷水解酵素作用的機制………………………7
1.4 目標物的合成策略…………………………………………9
第二章 結果與討論……………………………………………15
2.1 合成單一六圓環氮醣……………………………………15
2.2 六圓環氮醣衍生物…………………………………19
2.3 合成六圓環氮醣氮上有取代基及其衍生物…………………………21
2.4 合成雙醣氮醣…………………………………………………… 22
2.5 以乙醚當架橋合成双環氮醣………………………………………… 25
2.6 結論…………………………………………………………… 29
第三章 實驗部份……………………………………………………… 30
3.1 一般實驗方法…………………………………………………… 30
3.2 實驗步驟及光譜資料……………………………………………… 31
第四章 參考文獻……………………………………………… 59
附圖 化合物光譜圖

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