Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor

doi:10.6023/cjoc201801036

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1712-1717.DOI: 10.6023/cjoc201801036 Previous Articles Next Articles

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Selectfluor介导的高效高选择性地脱除叔丁氧羰基方法研究

曾逸杰^a, 段岳^a, 赵辉^b, 胡祥国^a

a 江西师范大学国家单糖化学合成工程技术研究中心南昌 330022;
b 安徽省应用技术研究院安徽省植物活性成分分离提取工程技术研究中心合肥 230031

收稿日期:2018-01-25 修回日期:2018-02-12 发布日期:2018-03-16
通讯作者: 赵辉, 胡祥国 E-mail:zh1986@iccas.ac.cn;huxiangg@iccas.ac.cn
基金资助:
国家自然科学基金（No.21502076）、江西省自然科学基金（No.20161BAB213068）、合肥市百人计划及江西省杰出青年基金（No.20171BCB23039）资助项目.

Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor

Zeng Yijie^a, Duan Yue^a, Zhao Hui^b, Hu Xiangguo^a

a National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022;
b Anhui Engineering Technology Research Center for Extraction and Isolation of Active Components, Anhui Academy of Applied Technology, Hefei 230031

Received:2018-01-25 Revised:2018-02-12 Published:2018-03-16
Contact: 10.6023/cjoc201801036 E-mail:zh1986@iccas.ac.cn;huxiangg@iccas.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502076), the Natural Science Foundation of Jiangxi Province (No. 20161BAB213068), the Hundred-Talent Program (Hefei) and the Outstanding Young Talent Program of Jiangxi Province (No. 20171BCB23039).

1. Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor.PDF(2070KB)

Abstract

Selectfluor, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2] octane bis(tetrafluoroborate), is among the most popular fluorinating reagents owning to its commercially availability and non-hygroscopic property. The discovery and understanding of new reactivities of selectfluor are thus important for reaction design and optimization when this popular reagent is employed. It has been found that selectfluor could selectively remove Boc group from doubly protected amines in acetonitrile. This deprotection could be of interest when compared to other reported methods, not only because selectfluor is a solid and easy-to-handle, but also because the reaction is mild, operationally simple and chemoselective. The potential usefulness of this method is demonstrated by the deprotection of a series of protected amino acids and a one-step synthesis of pharmaceutically important purine derivative. The NMR experiments conducted in CD₃CN explain why stoichiometric amount of selectfluor is needed for a successful reaction.

Key words: selectfluor, t-butyloxycarbonyl, deprotection, selectivity, synthesis

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Zeng Yijie, Duan Yue, Zhao Hui, Hu Xiangguo. Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor[J]. Chin. J. Org. Chem., 2018, 38(7): 1712-1717.

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Selectfluor介导的高效高选择性地脱除叔丁氧羰基方法研究

Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor

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