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



曾逸杰a, 段岳a, 赵辉b, 胡祥国a   

  1. 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;
  • 基金资助:


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

Zeng Yijiea, Duan Yuea, Zhao Huib, Hu Xiangguoa   

  1. 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;
  • 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).

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