將methyl α-D-glucopyranoside 1與D-ribose 5 為起始物，分別經過一些化學反應，成功地製備自由基接受者烯醇醚糖，如methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 4和methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside 8。化合物4、 8可以與經cericIV ammonium nitrate (CAN)誘導dimethyl malonate產生的自由基，分別與4、8進行自由基加成/氧化反應，由此反應製備更高碳糖類分子化合物9、10、12。

Enol ether sugars such as methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 4 and methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside 8 have been successfully prepared from methyl α-D-glucopyranoside 1 and D-ribose 5, respectively. Treatment of 4 and 8 with malonyl radical, which was generated from cericIV ammonium nitrate (CAN) and dimethyl malonate in methanol, afforded the desired higher — carbon sugars 9, 10 , and 12, respectively.

中文摘要----------------------------------------------------------i
英文摘要 ---------------------------------------------------------ii
目錄 -------------------------------------------------------------- iii
英文縮寫符號--------------------------------------------------vi
壹、 序論
一、簡介---------------------------------------------------------1
二、自由基化學反應-----------------------------------------2
(一) 一般性介紹 ---------------------------------------------- 2
(二) 前列分子軌域原理------------------------------------- 4
三、碳水化合物分子間自由基加成反應
(一)、六碳糖pyranosyl自由基加成反應-----------------7
(二)、五碳糖furanosyl自由基加成反應-----------------12
(三)自由基加成/氧化反應----------------------------------16
貳、 結果與討論
一、 製備自由基接受者的糖類分子--------------------20
二、 分子間自由基加成反應的研究--------------------24
三、 總結--------------------------------------------------------27
參、實驗部分
一、 測試儀器說明------------------------------------------28
二、 實驗進行所使用之儀器及溶劑的前處理------29
三、 化合物的製備及其光譜數據----------------------32
肆、參考資料-------------------------------------------------40
伍、附圖---------------------------------------------------44~70

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