Chinese Journal of Organic Chemistry >
Synthesis of Aryl or Heteroaryl C-Nucleosides by Direct Coupling of a Carbohydrate Moiety with a Preformed Aglycon Unit
Received date: 2021-04-16
Revised date: 2021-05-12
Online published: 2021-06-17
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
Feifan Li , Jin Qu . Synthesis of Aryl or Heteroaryl C-Nucleosides by Direct Coupling of a Carbohydrate Moiety with a Preformed Aglycon Unit[J]. Chinese Journal of Organic Chemistry, 2021 , 41(10) : 3948 -3964 . DOI: 10.6023/cjoc202104032
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