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

doi:10.6023/cjoc202104032

Abstract

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

Cite this article

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.

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Fig. & Tab. 51

Figure 1. Nature-occurring C-nucleosides

Figure 2. Structures of tiazofurin, TAD and NAD

Figure 3. Antiviral C-nucleoside drugs

Scheme 1. Synthesis of C-nucleosides by coupling of hemiacetal ribose with organometallic reagent

Scheme 2. Synthesis of pseudouridine by coupling of hemiacetal ribose with organolithium reagent

Scheme 3. Synthesis of C-nucleoside 14 by coupling of hemiacetal ribose with Grignard reagent

Scheme 4. Synthesis of pyrazole C-nucleosides 18 and 23 Reagents and conditions: (a) toluene, –20 ℃~r.t.; (b) 1.5 mol/L HCl, THF, reflux; (c) N,N,N',N'-tetramethylazodicarboxamide (TM- AD), Bu3P, THF, r.t.; (d) Pd(OH)2/C, cyclohexene

Scheme 5. Mechanism of Mitsunobu cyclization

Scheme 6. Synthesis of C-nucleosides by coupling of open- chain ribose with organometallic reagent

Scheme 7. Synthesis of C-nucleoside 27 by coupling of open- chain ribose with organolithium reagent

Scheme 8. Synthesis of C-nucleoside 31 by coupling of open- chain ribose with organolithium reagent

Scheme 9. Synthesis of C-nucleosides by coupling of 1,4-ribo- nolactone with organometallic reagent

Scheme 10. Synthesis of C-nucleoside 35 by coupling of 1,4- ribonolactone with organolithium reagent

Scheme 11. Synthesis of C-nucleosides 41, 44, 47, 51 and 52 by coupling of lactone with organometallic reagent

Scheme 12. Conformations of C(1')-phenyl furanosyl oxocarbenium ion

Scheme 13. Synthesis of C-nucleoside 57 by coupling of 1,4- ribonolactone with organolithium reagent Reagents and conditions: (a) n-BuLi, toluene, –78 ℃, 73%; (b) Et3SiH, BF3•Et2O, DCM, 0 ℃; (c) LiHMDS then Ac2O, toluene, r.t., 84% from 53; (d) Et3SiH, BF3•Et2O, DCM, 0 ℃, 81%; (e) n-BuLi, –78 ℃, then Ac2O, –78 ℃~r.t., 18%; (f) Et3SiH, BF3•Et2O, DCM, 0 ℃, 79%

Scheme 14. Synthesis of pseudouridine by coupling of ribonolactone with organolithium reagent

Scheme 15. Synthesis of C-nucleosides 64 and 67 by coupling of lactone with organocerium reagent

Scheme 16. Synthesis of C-nucleosides 70 and 74 by coupling of ribonolactone with organolithium reagent

Scheme 17. Synthesis of diaryl C-nucleosides 77 by coupling of ribonolactone with organolithium reagent

Scheme 18. Synthesis of 1'-substituted C-nucleosides 81 and 83 by coupling of ribonolactone with organolithium reagent

Scheme 19. Synthesis of pseudouridine by coupling of ribofuranosyl chloride with organolithium reagent

Scheme 20. Synthesis of C-nucleosides 44 and 90 by coupling of ribofuranosyl chloride with Grignard reagent

Scheme 21. Synthesis of C-nucleosides 91 and 93 by coupling of ribofuranosyl chloride with Grignard reagents

Scheme 22. PPh3-catalyzed cross-coupling of ribofuranosyl halides with Grignard reagents

Scheme 23. Proposed mechanism of PPh3-catalyzed cross- coupling reaction

Scheme 24. Synthesis of C-nucleosides 97~103 by coupling of ribofuranosyl chloride with cadmium organyls

Scheme 25. Synthesis of C-nucleosides 103~110 by coupling of ribofuranosyl chloride with cuprate reagents

Scheme 26. Synthesis of β-aryl-C-nucleosides from 1,2-anhy- drosugars

Scheme 27. Synthesis of C-nucleosides from furanoid glycals via Heck coupling reaction

Scheme 28. Synthesis of C-nucleoside 128 from furanoid glycals via Heck coupling reaction

Scheme 29. Synthesis of C-nucleosides 134 and 135 from furanoid glycals via Heck coupling reaction

Scheme 30. Synthesis of C-nucleoside 139 from unprotected furanoid glycals via Heck coupling reaction

Scheme 31. Synthesis of C-nucleoside 143 from furanoid gly- cals via Heck coupling reaction

Scheme 32. Synthesis of C-nucleoside 147 from furanoid glycals via Heck coupling reaction

Scheme 33. Synthesis of C-nucleosides 150 and 151 from furanoid glycols via Heck coupling reaction

Scheme 34. Synthesis of C-nucleoside 153 from ribofuranosyl chloride via Ni-catalyzed Negishi cross-coupling reaction

Scheme 35. Synthesis of C-nucleosides from ribofuranosyl halides via Co-catalyzed cross-coupling reaction

Scheme 36. Synthesis of C-nucleosides from ribofuranosyl chloride via Fe-catalyzed cross-coupling reaction

Scheme 37. Synthesis of C-nucleosides from ribofuranosyl chloride via Pd-catalyzed C(sp2)—H functionalization

Scheme 38. Synthesis C-nucleosides via the merger of photoredox and nickel catalysis

Scheme 39. Synthesis of C-nucleosides from hemiacetal ribose via Lewis acid catalyzed Friedel-Crafts reaction

Scheme 40. Synthesis of C-nucleosides from hemiacetal ribosevia Brønsted acid catalyzed Friedel-Crafts reaction

Scheme 41. Synthesis of C-nucleosides from ribofuranosyl bromide via Ag2O catalyzed Friedel-Crafts reaction

Scheme 42. Synthesis of C-nucleosides from ribofuranosyl chloride via Lewis acid catalyzed Friedel-Crafts reaction

Scheme 43. Synthesis of C-nucleosides from ribofuranosyl fluoride via Lewis acid catalyzed Friedel-Crafts reaction

Scheme 44. Synthesis of C-nucleosides from methoxyribose via Lewis acid catalyzed Friedel-Crafts reaction

Scheme 45. Synthesis of C-nucleosides via SnCl4 catalyzed Friedel-Crafts reaction

Scheme 46. Synthesis of C-nucleosides from tetraacetateribose via Lewis acid catalyzed Friedel-Crafts reaction

Scheme 47. Synthesis of C-nucleoside 208 from tetraacetateribose and 2-trimethylsilyl thiazole catalyzed by SnCl4

Scheme 48. Synthesis of C-nucleoside 210 from ribofuranosyl trichloroacetimidate via Lewis acid catalyzed Friedel-Crafts reaction

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