臺灣博碩士論文加值系統

我們利用2-C-hydroxymethylglucal和在對位有烷基、烷氧基、氯和酯基等各種芳香硼酸加入0.5當量的醋酸鈀進行Suzuki-Miyaura反應；而這些醣加成的產物（C-aryl glycosides）具有高度立體選擇性，並且可在1小時內完成反應，產率為63-83%。
然而，當我們將此條件應用到2-甲苯硼酸，2-甲基氧硼酸和2-溴基硼酸，則沒有得到預期的β-C-aryl glycosides，而是得到α位向的C-aryl glycosides，其產率為62-72%。此合成策略也應用於2-C-hydroxymethyl galactal和4-苯環硼酸、4-甲苯硼酸和4-乙基苯硼酸。可惜，得到的是外消旋的C-aryl glycosides混合物。

We applied the Suzuki-Miyaura reaction of 2-C-hydroxymethyl glucal with various arylboronic acid bearing an alkyl, alkoxy, cholor, and ester groups at the para position in the presence of 0.5 equiv of palladium(II) acetate. The glycosyl additions gave the high stereoselective β-C-aryl glycosides and were complete in 1 h in 63–83% yield.
However, when we applied this method to 2-tolyboronic acid, 2-methoxyphenylboronic acid, and 2-bromophenylboronic acid, the corresponding β-C-aryl glycosides cannot be obtained and the α-C-aryl glycosides was found in 62-72% yield. The synthetic strategy was also applicable to 2-C-hydroxymethyl galactal with 4-benzeneboronic acid, 4-tolyboronic acid and 4-ethylphenylboronic acid. Unfortunately, the racemic C-aryl glycosides were provided.

表目錄 II
圖目錄 III
中文摘要 V
英文摘要 VI
第一章 緒論 1
第二章 研究目的與動機 8
第三章 結果與討論 9
3.1、化合物26a-c製備 9
3.2、endo-glucal進行Suzuki-Miyaura反應 10
3.3、Arylboronic acid之苯環取代基對Suzuki-Miyaura反應的影響 13
3.4、endo-galactal進行Suzuki-Miyaura 反應 22
3.5、反應機轉的推導 28
第四章 結論 30
第五章 實驗部分 31
第一節　試藥、溶媒及材料 31
第二節　貴重儀器 35
第三節　化合物製備 37
一、 1-(3,4,6-tri-O-benzyl-2-deoxy-2-C-formyl-β-D-mannopyranosyl)-aryl benzene衍生物28-50合成 37
二、 1-(3,4,6-tri-O-methyl-2-deoxy-2-C-formyl-β-D-mammopyranosl) -aryl benzene衍生物51-54合成 46
三、 1-(3,4,6-tri-O-benzyl-2-deoxy-2-C-formyl-D-galactopyra-nosyl)-aryl benzene衍生物54-56合成 49
四、 1-(3,4,6-tri-O-benzyl-2-deoxy-2-C-formyl-D-galactopyranosyl)-aryl benzene衍生物54-56混合物分離 52
參考文獻 57
附　錄 59

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