Citation: Yan Lianhai, Hou Yuheng, Li Xiaoliu, Chen Hua. Concise Synthesis of Furanosyl Benzimidazole C-Nucleosides by Mitsunobu Reaction[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3332-3337. doi: 10.6023/cjoc201806025 shu

Concise Synthesis of Furanosyl Benzimidazole C-Nucleosides by Mitsunobu Reaction

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002

Corresponding author: Li Xiaoliu, lixl@hbu.cn Chen Hua, hua-todd@163.com
Received Date: 15 June 2018
Revised Date: 21 August 2018
Available Online: 5 December 2018
Fund Project: the National Natural Science Foundation of China 21372060the National Natural Science Foundation of China 21772031Project supported by the National Natural Science Foundation of China (Nos. 21372060, 21772031)

Figures(5)

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.
- C-nucleoside,
- furanosyl benzimidazole,
- Mitsunobu reaction,
- regioselectivity
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