藉由氯化碘開發一個容易且有效之醣多-氧-乙醯化反應的方法

Studies on the Development of A Facile and Efficient Method for Per-O-Acetylation of Carbohydrates by Iodine Monochloride

蘇冠宇(Kuan-Yu Su)

指導教授 ： 蔡祐輔

中原大學/理學院/化學研究所/碩士(2015年)

https://doi.org/10.6840/cycu201500942

摘要

本篇論文旨在從事乙醯化反應 (acetylation)的開發研究，以應用在有機合成過程中，規劃以乙酸酐當作試劑，氯化碘 (ICl)作為催化劑對半乳糖G-1、G-3及化合物G-5、G-7 G-9進行醣多-氧-乙醯化反應，本反應其優點在於催化劑使用前毋須實施前處理，毋須使用額外溶劑，卻達到同樣效果，有效提升在有機合成過程中乙醯化反應的效率。
此外該反應所得產物的產率高。由實驗結果得知，G-1及G-3使用0.01當量氯化碘當催化劑，反應時間為1分鐘，產率達100%，而G-7及G-9使用0.01當量氯化碘時，因其立體障礙較大，反應時間為180分鐘，產率達86~88%。

關鍵字

乙醯化 ； 醣多-氧-乙醯化 ； 氯化碘

並列摘要

The primary concern of this study is to research in the acetylation reactions in organic synthesis, planning to use acetic anhydride as a reagent, iodine chloride (ICl) as a catalyst for the G-1, G-3, G-5, G-7 and G-9 to react per-O-acetylation reaction of carbohydrates, this reaction has the advantage that without the pre-treatment before use catalyst, none of additional solvents, and also can achieve the same effect, effectively reducing the organic synthesis process, improved acetylation reaction efficiency.
In addition, the reaction yield of the resulting product. From the experiment results that, G-1 and G-3 using 0.01 equivalents of iodine monochloride as catalyst, the reaction time is 1 minute, the yield was 100%, while the G-7 and G-9 using 0.01 equivalents of iodine monochloride as catalyst, because of its large steric hindrance, the reaction time is 180 minutes, the yield was 86 to 88%.

並列關鍵字

acetylation ； Per-O-Acetylation ； iodine monochloride

參考文獻

2.Kirk Othmer Encyclopedia of Chemical Technology, 3rd ed; John Wiley & Sons: New York, 1982; Vol. 19, p 464.

4.Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001, 1584.

6.Hyatt, J. A.; Tindall, G. W. Heterocycles 1993, 35, 227.

8.Kumareswaran, R.; Gupta, A.; Vankar, Y. D. Synth. Commun. 1997, 27, 277.

9.(a) Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342. (b) Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. Chem. Commun. 1996, 2625.