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

doi:10.6023/cjoc202104032

摘要/Abstract

C-核苷与自然界广泛存在的N-核苷的结构高度类似, 不同之处是C-核苷中核糖与碱基是通过碳-碳键连接的. C-核苷也可以被细胞内与N-核苷相关的酶所识别和利用, 从而抑制酶促的核酸的合成或降解, 进而抑制病毒或者癌细胞的增殖, 用于治疗2019新型冠状肺炎的C-核苷药物remdesivir的临床应用引起人们对C-核苷合成的关注. 由糖基供体和糖基配体直接偶联能高效合成芳基或杂芳基C-核苷, 从核糖衍生物与有机金属试剂的反应、过渡金属催化的核糖衍生物与有机金属试剂的反应、酸催化的核糖衍生物的傅克反应三种主要合成策略总结了近年来合成芳基或杂芳基C-核苷的文献方法, 每个反应类型中又分别从半缩醛核糖、核糖内酯、卤代核糖和核糖烯等不同糖供体角度展开讨论, 并对反应中α或β构型产物的生成机理进行了详细说明.

关键词: C-核苷, 抗病毒药物, Heck反应, 傅克反应

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

引用此文

李非凡, 渠瑾. 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[J]. 有机化学, 2021, 41(10): 3948-3964.

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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图/表 51

图1. 天然存在的C-核苷

Figure 1. Nature-occurring C-nucleosides

图2. Tiazofurin、TAD和NAD的结构

Figure 2. Structures of tiazofurin, TAD and NAD

图3. C-核苷抗病毒药物

Figure 3. Antiviral C-nucleoside drugs

图式1. 半缩醛核糖与有机金属试剂偶联合成C-核苷

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

图式2. 半缩醛核糖与有机锂试剂偶联合成pseudouridine

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

图式3. 半缩醛核糖与格氏试剂偶联合成C-核苷14

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

图式4. 合成吡唑C-核苷18和23

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

图式5. Mitsunobu环化的机理

Scheme 5. Mechanism of Mitsunobu cyclization

图式6. 开环的核糖与有机金属试剂偶联合成C-核苷

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

图式7. 开环的核糖与有机锂试剂偶联合成C-核苷27

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

图式8. 开环的核糖与有机锂试剂偶联合成C-核苷31

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

图式9. 1,4-核糖内酯与有机金属试剂偶联合成C-核苷

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

图式10. 1,4-核糖内酯与有机锂试剂偶联合成C-核苷35

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

图式11. 核糖内酯与有机金属试剂偶联合成C-核苷41、44、47、51和52

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

图式12. C(1')-苯基核糖的氧鎓离子的构象

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

图式13. 1,4-核糖内酯与有机锂试剂偶联合成C-核苷57

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%

图式14. 核糖内酯与有机锂试剂偶联合成pseudouridine

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

图式15. 核糖内酯与有机铈试剂偶联合成C-核苷64和67

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

图式16. 核糖内酯与有机锂试剂偶联合成C-核苷70和74

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

图式17. 核糖内酯与有机锂试剂偶联合成二芳基取代的C-核苷77

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

图式18. 核糖内酯与有机锂试剂偶联合成C(1')位连有两个不同取代基的C-核苷81和83

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

图式19. 1'-氯核糖与有机锂试剂偶联合成pseudouridine

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

图式20. 1'-氯核糖与格氏试剂偶联合成C-核苷44和90

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

图式21. 1'-氯核糖与格氏试剂偶联合成C-核苷91和93

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

图式22. 三苯基膦催化的卤代核糖与格氏试剂的偶联反应

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

图式23. 三苯基膦催化的偶联反应的可能机理

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

图式24. 1'-氯脱氧核糖与有机镉试剂偶联合成C-核苷97~103

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

图式25. 1'-氯脱氧核糖与有机铜试剂偶联合成C-核苷103~110

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

图式26. 由1,2-脱水核糖合成β-C-萘基核苷

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

图式27. 由核糖烯经Heck反应合成C-核苷

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

图式28. 由核糖烯经Heck反应合成C-核苷128

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

图式29. 由核糖烯经Heck反应合成C-核苷134和135

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

图式30. 由未保护核糖烯经Heck反应合成C-核苷139

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

图式31. 由核糖烯经Heck反应合成C-核苷143

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

图式32. 由核糖烯经Heck反应合成C-核苷147

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

图式33. 由核糖烯经Heck反应合成C-核苷150和151

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

图式34. 由1'-氯核糖经镍催化的Negishi反应合成C-核苷153

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

图式35. 钴催化的卤代核糖的偶联反应合成C-核苷

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

图式36. 铁催化的1'-氯核糖的偶联反应合成C-核苷

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

图式37. 由1'-氯核糖经钯催化的C(sp2)—H官能团化合成C-核苷

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

图式38. 通过光氧化还原和镍催化合成C-核苷

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

图式39. 由半缩醛核糖经路易斯酸催化的傅克反应合成C-核苷

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

图式40. 半缩醛核糖经Brønsted酸催化的傅克反应合成C-核苷

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

图式41. 由溴代核糖经氧化银催化的傅克反应合成C-核苷

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

图式42. 由氯代核糖经路易斯酸催化的傅克反应合成C-核苷

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

图式43. 由氟代核糖经路易斯酸催化的傅克反应合成C-核苷

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

图式44. 由甲氧基核糖经路易斯酸催化的傅克反应合成C-核苷

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

图式45. SnCl4催化的傅克反应合成C-核苷

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

图式46. 由四乙酰核糖经路易斯酸催化的傅克反应合成C-核苷

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

图式47. SnCl4催化的由四乙酰核糖和2-三甲基硅基噻唑反应合成C-核苷208

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

图式48. 由核糖的三氯乙酰亚胺酯经路易斯酸催化的傅克反应合成C-核苷210

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

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