Mitsunobu反应简便合成呋喃糖基苯并咪唑C-核苷
收稿日期: 2018-06-15
修回日期: 2018-08-21
网络出版日期: 2018-09-05
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
Received date: 2018-06-15
Revised date: 2018-08-21
Online published: 2018-09-05
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21372060, 21772031).
以不保护的五、六元单糖与邻苯二胺反应，得到中间体多羟基链苯并咪唑.进一步，利用Mitsunobu反应，分子内脱水合成了构型翻转和构型保持的呋喃糖基苯并咪唑C-核苷.Mitsunobu反应良好的区域选择性，为呋喃糖基苯并咪唑C-核苷的合成提供一个有效方法.
关键词： C-糖苷; 呋喃糖基苯并咪唑; Mitsunobu反应; 区域选择性
闫连海 , 侯宇恒 , 李小六 , 陈华 . Mitsunobu反应简便合成呋喃糖基苯并咪唑C-核苷[J]. 有机化学, 2018 , 38(12) : 3332 -3337 . DOI: 10.6023/cjoc201806025
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.
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