Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3332-3337.DOI: 10.6023/cjoc201806025 Previous Articles     Next Articles

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Mitsunobu反应简便合成呋喃糖基苯并咪唑C-核苷

闫连海, 侯宇恒, 李小六, 陈华   

  1. 河北大学化学与环境科学学院 河北省化学生物学重点实验室 保定 071002
  • 收稿日期:2018-06-15 修回日期:2018-08-21 出版日期:2018-12-25 发布日期:2018-09-05
  • 通讯作者: 李小六, 陈华 E-mail:lixl@hbu.cn;hua-todd@163.com
  • 基金资助:

    国家自然科学基金(Nos.21372060,21772031)资助项目.

Concise Synthesis of Furanosyl Benzimidazole C-Nucleosides by Mitsunobu Reaction

Yan Lianhai, Hou Yuheng, Li Xiaoliu, Chen Hua   

  1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002
  • Received:2018-06-15 Revised:2018-08-21 Online:2018-12-25 Published:2018-09-05
  • Contact: 10.6023/cjoc201806025 E-mail:lixl@hbu.cn;hua-todd@163.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21372060, 21772031).

Tetri/pentitolyl benzimidazoles were prepared by using the unprotected monosaccharides and o-phenylenediamine as the starting materials. Intramolecular dehydration of the oligotoltyl benzimidazoles afforded two furanosyl benzimidazole C-nucleosides (α/β isomers) through Mitsunoble reaction. One isomer was the configuration-retension product, the other was the configuration-inversion one. The regioselectivity of Mitsunobu reaction is good, which provides an effective protocol for the synthesis of furanosyl benzimidazole C-nucleosides.

Key words: C-nucleoside, furanosyl benzimidazole, Mitsunobu reaction, regioselectivity