臺灣博碩士論文加值系統

雖然過去有許多製備exo-glycals的方法，但是總要進行複雜的反應，或是無法得到理想的產率。本論文以便宜且容易取得的醣內酯為起始物進行親核性加成反應，然後加入三氟醋酸酐及吡啶進行脫水反應，可以得到一系列具有良好產率以及位向選擇性的exo-glycals，這裡面包含了gluco-、manno-、以及galacto-type的五員環、六員環、以及各種不同的取代基的exo-glycals。本論文接著探討這類分子化學反應性及生物活性，得到了以下的結論：
1.雖然exo-glycals具有半椅狀的結構，其環上的氧原子也有可能因共振而帶有部分正電荷，然而經過測試後，發現exo-glycals並非好的醣水解酵素抑制劑。
2.在歸納酸催化醇類對exo-glycals進行加成反應的結果發現，sugar diene的反應性會比,-unsaturated esters的反應性差，而manno-type exo-glycals的反應性會比gluco-以及galacto-type的反應性還要好。此外，醇類結構的立體障礙大小會明顯影響加成的反應時間及產率。
3.對exo-glycals進行氫硼化加成反應，可以成功獲得產率良好的homoallylic alcohols、spiroacetals以及acetogenins等具有生物活性物質的前趨物。

The reactivity of exo-glycals have not been well studied due to their tedious preparation procedures with low yields. Herein we developed a synthetic strategy to use sugar lactones as starting material. After nucleophilic addition and subsequent dehydration with trifluoroacetic anhydride and pyridine, a series of exo-glycals could be obtained with high yield. These exo-glycals included gluco-、manno-、and galacto-configuration furanoses or pyranoses. The biological and chemical reactivity were studied and summarized as follow.
1.Although the partial positive charge may possibly generate on the ring oxygen and the conformation of exo-glycals is half-chaired, the resulting molecules did not show significant inhibition for - and - glucosidases.
2.As for the intermolecular alcohol addition of exo-glycals, the reactivity of exo-glycals esters was better than that of sugar dienes. The reactivity of manno-type exo-glycals was better than that of gluco- and galacto-types. The stereo hindrance of alcohols was observed to play an important role in the addition reactions.
3.The hydroboration of exo-glycals was able to produce bio-active molecules with good yields, including homoallylic alcohols, spiroacetals, and acetogenins.

第一章 緒論……………………………………………1
第一節 醣水解酵素…………………………………5
第二節 醣內酯………………………………………7
第三節 Glycals………………………………………9
1-3-1. endo-Glycals……………………………9
1-3-2. exo-Glycals………………………………12
1-3-3. Conjugated exo-Glycals………………14
第四節 具有生物活性之分子……………..…………15
1-4-1. Spiroacetals……………..………………15
1-4-2. Acetogenins……………..………………19
1-4-3. C-glycosides……………..………………20
第五節 研究目的………………………..……………22
第二章 結果與討論……………………………………25
第一節 製備全保護醣內酯…………………………25
2-1-1. 製備TBDMS全保護醣內酯……………25
2-1-2. 製備benzyl全保護醣內酯……………27
第二節 exo-Glycals之製備及酵素測試……………28
2-2-1. 醣內酯的親核性加成反應………………28
2-2-2. 製備Sugar Dienes………………………32
2-2-3. 酵素合成雙醣……………………………38
2-2-4. 製備,-unsaturated esters……………39
2-2-5. 醣水解酵素抑制測試……………………40
2-2-6. 製備,-unsaturated aldehydes………42
第三節 exo-Glycals分子間及分子內醇類加成反應……44
2-3-1. exo-Glycals分子間醇類加成反應…………45
2-3-2. exo-Glycals分子間醇類加成反應-製備Spiroacetals………………………………53
第四節 合成具有生物活性分子之骨架……………61
2-4-1. 製備Homoallylic alcohols………………61
2-4-2. 製備Acetogenin building blocks………69
2-4-3. 製備C-glycosides…………………………71
第五節 結論…………………………………………72
第三章 實驗部分………………………………………75
第一節 實驗儀器……………………………………75
第二節 實驗步驟及光譜數據………………………77
第四章 參考資料………………………………………153
第五章 附錄……………………………………………164

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