本文描述了碳環核苷的發展過程，同時也描述了將不同環融合在五元碳環上的方法來對碳環核苷的構象進行鎖定。 / 以D-核糖為起始原料，經過12 步反應並以分子內的Diels-Alder 反應 (IMDA)為關鍵步驟合成出了關鍵的中間體192，它的總產率為27%。通過對中間體192中的環己烯的結構進行修飾，經過3-4 步反應成功合成出了7 個具有雙環[4.3.0]壬烷結構的碳環核苷（185-191），它們的構型也通過其X 光單晶結構圖來進行確定。[附圖] / 以一價銅催化端炔和疊氮化物的Huisgen 環加成反應為關鍵步驟，成功地合成出了12 個具有雙環[4.3.0]壬烷結構的碳環三唑核苷。[附圖] / 同時，我們也合成12 個具有雙環[4.3.0]壬烷結構的碳環三唑核苷羧酸。[附圖] / 另外，我們也合成出了两個在三唑環上含有羧酸的碳環三唑核苷（298 和 299）。[附圖] / 最後，我們還合成出了16 個含有大基團叔丁基羧酸酯的碳環三唑核苷(260-263, 273-276, 286-289 和294-297)。[附圖] / In this thesis, a review regarding the development of carbobicyclic nucleosides and conformationally locked carbobicyclic nucleosides by fusing different rings onto the five-member ring was presented. / The key intermediate 192 was synthesized from D-ribose in 12 steps with 27% overall yield, using an Intramolecular Diels-Alder reaction (IMDA) as the key step. By modification of the cyclohexene ring, seven carbobicyclic adenosine analogues 185-191 with a bicyclo[4.3.0]nonane framework were prepared successfully from intermediate 192 in 3 to 4 steps and their conformations were examined by X-ray crystallography [with diagram]. / Twelve carbobicyclic ribavirin analogues 232-239 and 250-253 with a bicyclo[4.3.0]nonane framework were synthesized successfully by using a copper catalyzed azide-alkyne cycloaddition (Huigsen reaction) as the key step [with diagram]. / Another twelve ribavirin analogues bearing a carboxylate group (264-267, 277-280 and 290-293) with a bicyclo[4.3.0]nonane framework were also obtained [with diagram]. / Furthermore, two more ribavirin analogues bearing a carboxylic acid in triazole (298 and 299) with a bicyclo[4.3.0]nonane framework were obtained. [with diagram] / Finally, twelve ribavirin analogues bearing a tert-butyl carboxylate ester (260-263, 273-276, 286-289 and 290-293) with a bicyclo[4.3.0]nonane framework were also obtained [with diagram]. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Detailed summary in vernacular field only. / Li, Fanglin. / Thesis (Ph.D.) Chinese University of Hong Kong, 2015. / Includes bibliographical references (leaves 175-187). / Abstracts also in Chinese.
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_1077742 |
| Date | January 2015 |
| Contributors | Li, Fanglin (author.), Shing, Kung Ming Tony (thesis advisor.), Chinese University of Hong Kong Graduate School. Division of Chemistry. (degree granting institution.) |
| Source Sets | The Chinese University of Hong Kong |
| Language | English, Chinese |
| Detected Language | English |
| Type | Text, bibliography, text |
| Format | electronic resource, electronic resource, remote, 1 online resource (xi, 325 leaves) : illustrations (some color), computer, online resource |
| Rights | Use of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/) |
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