Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 3948-3964.DOI: 10.6023/cjoc202104032 Previous Articles     Next Articles

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由糖基供体和糖基配体直接合成芳基或杂芳基C-核苷的研究进展

李非凡, 渠瑾*()   

  1. 南开大学化学学院 元素有机化学国家重点实验室 天津 30071
  • 收稿日期:2021-04-16 修回日期:2021-05-12 发布日期:2021-06-17
  • 通讯作者: 渠瑾
  • 基金资助:
    国家自然科学基金(21772105)

Synthesis of Aryl or Heteroaryl C-Nucleosides by Direct Coupling of a Carbohydrate Moiety with a Preformed Aglycon Unit

Feifan Li, Jin Qu()   

  1. State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
  • Received:2021-04-16 Revised:2021-05-12 Published:2021-06-17
  • Contact: Jin Qu
  • Supported by:
    National Natural Science Foundation of China(21772105)

C-Nucleosides have similar structure compared to native N-nucleosides, while the carbohydrate unit and the base in a C-nucleoside are connected through a carbon-carbon bond. Because they can also be recognized and utilized by enzymes associated with N-nucleosides in cells, C-nucleosides can inhibit enzyme-catalyzed synthesis or degradation of nucleic acids, thereby inhibiting the proliferation of viruses or cancer cells. C-Nucleoside synthesis has drawn much attention since the clinical application of the C-nucleoside drug remdesivir for the treatment of COVID-19. The direct coupling of a carbohydrate moiety with a preformed aglycon unit is an efficient synthetic approach to construct aryl or heteroaryl C-nucleoside. The synthetic methods of aryl or heteroaryl C-nucleosides in recent years are summarized from three main synthetic strategies: coupling of ribose derivatives with organometallic reagents, transition metal-catalyzed coupling of ribose derivatives with organometallic reagents, and acid-catalyzed Friedel-Crafts reaction of ribose derivatives. Each synthetic strategy is categorized in terms of sugar donor precursors, including hemiacetal riboses, ribonolactones, ribofuranosyl halides, glycal, and others. The mechanism of α or β product formation in these reactions are explained in detail as well.

Key words: C-nucleoside, antiviral drug, Heck reaction, Friedel-Crafts reaction