Citation: Yuhan Zhang, Xiao-Lin Zhang, Han Ding, Yuan Xu, Xue-Wei Liu. Catalytic ring-strain release toward a facial and efficient synthesis of versatile C-glycosides[J]. Chinese Chemical Letters, ;2025, 36(7): 110560. doi: 10.1016/j.cclet.2024.110560 shu

Catalytic ring-strain release toward a facial and efficient synthesis of versatile C-glycosides

Yuhan Zhang ^{a, b, 1} ,
Xiao-Lin Zhang ^{a, 1} ,
Han Ding ^{a, 1} ,
Yuan Xu ^a ,
Xue-Wei Liu ^{a, *,}

a.
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
b.
Collaborative Initiatives, Interdisciplinary Graduate Programme, Nanyang Technological University, Singapore 637335, Singapore

xuewei@ntu.edu.sg

Received Date: 2 August 2024
Revised Date: 4 October 2024
Accepted Date: 16 October 2024
Available Online: 18 October 2024

Figures(5)

C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values, whereas the access to the versatile structural analog of C-glycosides is a significant challenge to their advancement as therapeutic agents. We herein disclose a facial and efficient catalytic C-glycosylation using a glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate (CCBz) as the donor. The trailblazing glycosyl donor can be simply activated by a non-toxic and easily accessible Sc(Ⅲ) catalyst. The ring-strain release of the incorporated donor-acceptor cyclopropane (DAC) serves as a powerful driving force of the glycosylation system. The adaptability of current methods to different types of donors and acceptors was exemplified. Examinations on the synthetic potential were done with the one-pot synthesis of free C-indolyl-glycosides and the subsequent biological studies, unlocking the antibacterial potentials of these compounds.
- C-glycoside,
- Ring-strain release,
- Donor-acceptor cyclopropane,
- C-glycosylation,
- C-glycosidic bond
1. [1]
  C.J. Thibodeaux, C.E. Melançon, H. Liu, Angew. Chem. Int. Ed. 47 (2008) 9814–9859. doi: 10.1002/anie.200801204
2. [2]
  R.W. Gantt, P. Peltier-Pain, J.S. Thorson, Nat. Prod. Rep. 28 (2011) 1811–1853. doi: 10.1039/c1np00045d
3. [3]
  B. Cobucci-Ponzano, M. Moracci, Nat. Prod. Rep. 29 (2012) 697–709. doi: 10.1039/c2np20032e
4. [4]
  C.J. Thibodeaux, C.E. Melancon, H. Liu, Nature 446 (2007) 1008–1016. doi: 10.1038/nature05814
5. [5]
  J. Harle, S. Gunther, B. Lauinger, et al., Chem. Biol. 18 (2011) 520–530.
6. [6]
  T. Bililign, B.R. Griffith, J.S. Thorson, Nat. Prod. Rep. 22 (2005) 742–760. doi: 10.1039/b407364a
7. [7]
  K. Lalitha, K. Muthusamy, Y.S. Prasad, P.K. Vemula, S. Nagarajan, Carbohydr. Res. 402 (2015) 158–171.
8. [8]
  U. Hacksell, G.D. Jr Daves, Prog. Med. Chem. 22 (1985) 1–65.
9. [9]
  S.I. Elshahawi, K.A. Shaaban, M.K. Kharel, J.S. Thorson, Chem. Soc. Rev. 44 (2015) 7591–7697.
10. [10]
  É. Bokor, S. Kun, D. Goyard, et al., Chem. Rev. 117 (2017) 1687–1764. doi: 10.1021/acs.chemrev.6b00475
11. [11]
  Y. Yang, B. Yu, Chem. Rev. 117 (2017) 12281–12356. doi: 10.1021/acs.chemrev.7b00234
12. [12]
  M.M. Nielsen, C.M. Pedersen, Chem. Rev. 118 (2018) 8285–8358. doi: 10.1021/acs.chemrev.8b00144
13. [13]
  B. Liu, D. Liu, X. Rong, et al., Angew. Chem. Int. Ed. 62 (2023) e202218544.
14. [14]
  J.R. Romeo, J.D. Lucera, D. Jensen, L.M. Davis, C.S. Bennett, Org. Lett. 25 (2023) 3760–3765. doi: 10.1021/acs.orglett.3c01228
15. [15]
  T. Miura, M. Yoritate, G. Hirai, Chem. Commun. 59 (2023) 8564–8567. doi: 10.1039/d3cc02361c
16. [16]
  Q.Q. Mu, A.X. Guo, X. Cai, et al., Org. Lett. 25 (2023) 7040–7045. doi: 10.1021/acs.orglett.3c02624
17. [17]
  M. Zeng, C. Yu, Y. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202300424.
18. [18]
  X. Xiao, P. Han, J.P. Wan, J. Liu, Org. Lett. 25 (2023) 7170–7175. doi: 10.1021/acs.orglett.3c02688
19. [19]
  G. Zhao, U. Mukherjee, L. Zhou, et al., CCS Chem. 5 (2023) 106–116. doi: 10.31635/ccschem.022.202202282
20. [20]
  L. Yuan, Y. Fang, Z. Zhou, et al., Org. Lett. 25 (2023) 4394–4399. doi: 10.1021/acs.orglett.3c01605
21. [21]
  X.G. Liu, Q. Yang, D.Y. Liu, et al., Org. Lett. 25 (2023) 5022–5026. doi: 10.1021/acs.orglett.3c01691
22. [22]
  Y. Xia, Y. Wang, Z. Zhang, et al., Org. Lett. 25 (2023) 6741–6745. doi: 10.1021/acs.orglett.3c02601
23. [23]
  S. Hubner, J.G. de Vries, V. Farina, Adv. Synth. Catal. 358 (2016) 3–25. doi: 10.1002/adsc.201500846
24. [24]
  Y. Jiang, Y. Zhang, B.C. Lee, M.J. Koh, Angew. Chem. Int. Ed. 62 (2023) e202305138.
25. [25]
  Z. Azeem, P.K. Mandal, Adv. Synth. Catal. 365 (2023) 2818–2849. doi: 10.1002/adsc.202300425
26. [26]
  J. Wu, R. Purushothaman, F. Kallert, S.L. Homolle, L. Ackermann, ACS Catal. 14 (2024) 11532–11544. doi: 10.1021/acscatal.4c02322
27. [27]
  M.Y. Lyu, S.A. Jacobo, M.K. Brown, J. Am. Chem. Soc. 146 (2024) 18866–18872. doi: 10.1021/jacs.4c06246
28. [28]
  H. Shi, G. Yin, X. Lu, Y. Li, Chin. Chem. Lett. 35 (2024) 109674.
29. [29]
  C. Yu, Y. Xu, M. Zeng, et al., Adv. Sci. 11 (2024) 2307226.
30. [30]
  Y. Miyamoto, S. Murakami, Y. Sumida, G. Hirai, H. Ohmiya, Chem. Eur. J. 30 (2024) e202402256.
31. [31]
  L. Zhang, W. Zeng, D. Xie, J. Li, X. Ma, Org. Lett. 26 (2024) 1332–1337. doi: 10.1021/acs.orglett.3c04159
32. [32]
  D.Y. Liu, P.F. Wang, X.Y. Hu, et al., Org. Chem. Front. 11 (2024) 3609–3613.
33. [33]
  Y. Jiang, Y. Wei, Q.Y. Zhou, et al., Nature 631 (2024) 319–327.
34. [34]
  Q. Wang, Q. Sun, Y. Jiang, et al., Nat. Synth. 1 (2022) 235–244.
35. [35]
  C. Zhang, S.Y. Xu, H. Zuo, et al., Nat. Synth. 2 (2023) 251–260. doi: 10.1038/s44160-022-00214-1
36. [36]
  Q. Wang, B.C. Lee, T.J. Tan, et al., Nat. Synth. 1 (2022) 967–974. doi: 10.1038/s44160-022-00162-w
37. [37]
  W. Ye, C.M. Stevens, P. Wen, C.J. Simmons, W. Tang, J. Org. Chem. 85 (2020) 16218–16225. doi: 10.1021/acs.joc.0c01041
38. [38]
  M. Liu, B.H. Li, T. Li, et al., Org. Biomol. Chem. 18 (2020) 3043–3046. doi: 10.1039/d0ob00561d
39. [39]
  X. Chen, Q. Wang, B. Yu, Chem. Commun. 52 (2016) 12183–12186.
40. [40]
  A. Dubey, A. Tiwari, P.K. Mandal, J. Org. Chem. 86 (2021) 8516–8526. doi: 10.1021/acs.joc.1c00698
41. [41]
  S. Halder, R.B. Addanki, S. Moktan, P.K. Kancharla, J. Org. Chem. 87 (2022) 7033–7055. doi: 10.1021/acs.joc.2c00093
42. [42]
  S. Halder, R.B. Addanki, P.K. Kancharla, J. Org. Chem. 88 (2023) 1844–1854. doi: 10.1021/acs.joc.2c02426
43. [43]
  H. Liu, Z.F. Liang, H.J. Liu, et al., J. Am. Chem. Soc. 145 (2023) 3682–3695. doi: 10.1021/jacs.2c13018
44. [44]
  X. Xiao, H. Ding, L.C. Peng, et al., CCS Chem. 5 (2023) 2910–2921. doi: 10.31635/ccschem.023.202202671
45. [45]
  H. Ding, J. Lyu, X.L. Zhang, X. Xiao, X.W. Liu, Nat. Commun. 14 (2023) 4010.
46. [46]
  H. Ding, J. Lyu, X.L. Zhang, et al., Chem. Sci. 15 (2024) 3711–3729. doi: 10.1039/d3sc06619c
47. [47]
  H. Ding, X.L. Zhang, A. Guo, et al., J. Am. Chem. Soc. 146 (2024) 11811–11822. doi: 10.1021/jacs.4c00537
48. [48]
  D. Yang, H. Ding, X.L. Zhang, et al., Org. Lett. 26 (2024) 4986–4991. doi: 10.1021/acs.orglett.4c01637
49. [49]
  H. Zhang, A. Guo, H. Ding, et al., Org. Chem. Front. 11 (2024) 4470–4478. doi: 10.1039/d4qo00410h
50. [50]
  T. Hosoya, Y. Ohashi, T. Matsumoto, K. Suzuki, Tetrahedron Lett. 37 (1996) 663–666.
51. [51]
  Y. Wu, Z.X. Zhang, H. Hu, et al., Fitoterapia 82 (2011) 288–292.
52. [52]
  C.F. Liu, Molecules 27 (2022) 7439. doi: 10.3390/molecules27217439
53. [53]
  P. Kumari, V.S. Mishra, C. Narayana, et al., Sci. Rep. 10 (2020) 6660.
54. [54]
  R. Sangwan, Z. Azeem, P.K. Mandal, Adv. Synth. Catal. 366 (2024) 1484–1508. doi: 10.1002/adsc.202301490
55. [55]
  R. Mao, S. Xi, S. Shah, et al., J. Am. Chem. Soc. 143 (2021) 12699–12707. doi: 10.1021/jacs.1c05567
1. [1]
  Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
2. [2]
  Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2024.100463
3. [3]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
4. [4]
  Shuqi Chen , Cankun Zhang , Xiaonuo Dong , Hui-Jun Zhang , Jianbin Lin . Synthesis and photophysical properties of alternating donor-acceptor conjugated nanorings. Chinese Chemical Letters, 2025, 36(6): 110354-. doi: 10.1016/j.cclet.2024.110354
5. [5]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
6. [6]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
7. [7]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
8. [8]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
9. [9]
  Zhaoyue Lü , Tiantian Chai , Yichao Jin , Xiao Wang , Ye Zou , Lijiang Zhang , Jiankang Feng , Mengtong Zhang , Shuo Wang , Chichong Lu , Guofan Jin . Asymmetrical carbazole-benzonitrile-based TADF emitters designed by alternate donor-acceptor strategy. Chinese Chemical Letters, 2025, 36(6): 110817-. doi: 10.1016/j.cclet.2025.110817
10. [10]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
11. [11]
  Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO₂ and NH₃. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
12. [12]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
13. [13]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
14. [14]
  Jiawei Li , Cheng Chen , Mingyan Wu . Donor-acceptor type organic cocrystals for deep-red circularly polarized luminescence and two-photon excited emission. Chinese Journal of Structural Chemistry, 2025, 44(3): 100513-100513. doi: 10.1016/j.cjsc.2025.100513
15. [15]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
16. [16]
  Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
17. [17]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
18. [18]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
19. [19]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
20. [20]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(3)
HTML views(1)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142