Citation: Hongjin Shi, Guoyin Yin, Xi Lu, Yangyang Li. Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals[J]. Chinese Chemical Letters, ;2024, 35(12): 109674. doi: 10.1016/j.cclet.2024.109674 shu

Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals

Hongjin Shi ^a ,
Guoyin Yin ^{a, *,} ,
Xi Lu ^{b, *,} ,
Yangyang Li ^{a, *,}

a.
The Institute for Advanced Studies, Wuhan University, Wuhan 430072, China
b.
School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China

yinguoyin@whu.edu.cn

luxi@mail.ustc.edu.cn

yangyangl@whu.edu.cn

Received Date: 31 October 2023
Revised Date: 7 February 2024
Accepted Date: 22 February 2024
Available Online: 29 February 2024

Figures(3)

2-Deoxy-α-C-Glycosides are a significant class of carbohydrates found in numerous bioactive molecules and medicines. Developing a concise strategy for the assembly of these α-configured C-glycosides is crucial in the field of carbohydrate chemistry. However, current methods are restricted to the utilization of glycosyl radical precursors, which are required for pre-syntheses. Herein, we present a novel approach for the synthesis of 2-deoxy-α-C-glycosides using a nickel-catalyzed stereoselective coupling reaction with commercially available glycals. Notably, this method circumvents the preparation for diverse glycosyl radical precursors. The developed protocol exhibits a broad substrate scope and remarkable stereoselectivity under mild reaction conditions. Furthermore, the raw materials required for this process are readily accessible, eliminating the necessity for pre-functionalization modifications of the glycosyl substrates and ensuring high atomic economy.
- Nickel catalysis,
- Stereoselectivity,
- 2-Deoxy-α-C-glycosides,
- Glycals,
- Cross-coupling reaction
1. [1]
  V. Křen, J. Thiem, Chem. Soc. Rev. 26 (1997) 463–473. doi: 10.1039/CS9972600463
2. [2]
  S. Hanashima, B. Castagner, D. Esposito, et al., Org. Lett. 9 (2007) 1777–1779. doi: 10.1021/ol0704946
3. [3]
  S.A. Borisova, H.J. Kim, X. Pu, et al., ChemBioChem 9 (2008) 1554–1558. doi: 10.1002/cbic.200800155
4. [4]
  Y. Fujimoto, T. Hattori, S. Uno, et al., Carbohydr. Res. 344 (2009) 972–978. doi: 10.1016/j.carres.2009.03.006
5. [5]
  S. Muthana, H. Cao, X. Chen, Curr. Opinion Chem. Biol. 13 (2009) 573–581. doi: 10.1016/j.cbpa.2009.09.013
6. [6]
  P. Nagorny, B. Fasching, X. Li, et al., J. Am. Chem. Soc. 131 (2009) 5792–5799. doi: 10.1021/ja809554x
7. [7]
  M.H.D. Postema, Tetrahedron 48 (1992) 8545–8599. doi: 10.1016/S0040-4020(01)89435-7
8. [8]
  D.Y.W. Lee, M. He, Curr. Topics Med. Chem. 5 (2005) 1333–1350. doi: 10.2174/156802605774643042
9. [9]
  M. Ferrero, V. Gotor, Chem. Rev. 100 (2000) 4319–4348. doi: 10.1021/cr000446y
10. [10]
  M. Adamo, R. Pergoli, Curr. Org. Chem. 12 (2008) 1544–1569. doi: 10.2174/138527208786786318
11. [11]
  Y. Yang, B. Yu, Chem. Rev. 117 (2017) 12281–12356. doi: 10.1021/acs.chemrev.7b00234
12. [12]
  P. Hultin, Curr. Top. Med. Chem. 5 (2005) 1299–1331. doi: 10.2174/156802605774643015
13. [13]
  K. Kitamura, Y. Ando, T. Matsumoto, et al., Chem. Rev. 118 (2018) 1495–1598. doi: 10.1021/acs.chemrev.7b00380
14. [14]
  W. Shang, R. Shi, D. Niu, Chin. J. Chem. 41 (2023) 2217–2236. doi: 10.1002/cjoc.202300153
15. [15]
  E. De Clercq, J. Med. Chem. 59 (2016) 2301–2311. doi: 10.1021/acs.jmedchem.5b01157
16. [16]
  H. Liao, J. Ma, H. Yao, et al., Org. Biomol. Chem. 16 (2018) 1791–1806. doi: 10.1039/C8OB00032H
17. [17]
  P. Compain, O.R. Martin, Bioorg. Med. Chem. 9 (2001) 3077–3092. doi: 10.1016/S0968-0896(01)00176-6
18. [18]
  W. Zou, Curr. Top. Med. Chem. 5 (2005) 1363–1391. doi: 10.2174/156802605774642999
19. [19]
  M. Hocek, Chem. Rev. 109 (2009) 6729–6764. doi: 10.1021/cr9002165
20. [20]
  E. Leclerc, X. Pannecoucke, M. Ethève-Quelquejeu, et al., Chem. Soc. Rev. 42 (2013) 4270–4283. doi: 10.1039/C2CS35403A
21. [21]
  F. Zhu, M.J. Rourke, T. Yang, et al., J. Am. Chem. Soc. 138 (2016) 12049–12052. doi: 10.1021/jacs.6b07891
22. [22]
  C.C.J. Loh, Nat. Rev. Chem. 5 (2021) 792–815. doi: 10.1038/s41570-021-00324-y
23. [23]
  K.M. Hoang, N.R. Lees, S.B. Herzon, J. Am. Chem. Soc. 143 (2021) 2777–2783. doi: 10.1021/jacs.0c11262
24. [24]
  V.U.B. Rao, C. Wang, D.P. Demarque, et al., Nat. Chem. 15 (2022) 424–435.
25. [25]
  Q. Li, S.M. Levi, C.C. Wagen, et al., Nature 608 (2022) 74–79. doi: 10.1038/s41586-022-04958-w
26. [26]
  C. Zhang, S.Y. Xu, H. Zuo, et al., Nat. Synth. 2 (2023) 251–260. doi: 10.1038/s44160-022-00214-1
27. [27]
  L. Krasnova, C.H. Wong, J. Am. Chem. Soc. 141 (2019) 3735–3754. doi: 10.1021/jacs.8b11005
28. [28]
  K. Kanagaraj, J. Rebek, Y. Yu, Green Synth. Catal. 4 (2023) 7–9. doi: 10.1016/j.gresc.2022.10.005
29. [29]
  P.R. Schreiner, Chem. Soc. Rev. 32 (2003) 289–296. doi: 10.1039/b107298f
30. [30]
  S.J. Connon, Chem. Eur. J. 12 (2006) 5418–5427. doi: 10.1002/chem.200501076
31. [31]
  A.G. Doyle, E.N. Jacobsen, Chem. Rev. 107 (2007) 5713–5743. doi: 10.1021/cr068373r
32. [32]
  Y. Takemoto, Chem. Pharm. Bull. 58 (2010) 593–601. doi: 10.1248/cpb.58.593
33. [33]
  D. Larsen, L.M. Langhorn, O.M. Akselsen, et al., Chem. Sci. 8 (2017) 7978–7982. doi: 10.1039/C7SC03366D
34. [34]
  Y. Park, K.C. Harper, N. Kuhl, et al., Science 355 (2017) 162–166. doi: 10.1126/science.aal1875
35. [35]
  Q. Li, S.M. Levi, E.N. Jacobsen, J. Am. Chem. Soc. 142 (2020) 11865–11872. doi: 10.1021/jacs.0c04255
36. [36]
  A. Chen, B. Yang, Z. Zhou, et al., Chem. Catal. 2 (2022) 3430–3470. doi: 10.1016/j.checat.2022.10.019
37. [37]
  H. Gong, R. Sinisi, M.R. Gagné, J. Am. Chem. Soc. 129 (2007) 1908–1909. doi: 10.1021/ja068950t
38. [38]
  H. Gong, M.R. Gagné, J. Am. Chem. Soc. 130 (2008) 12177–12183. doi: 10.1021/ja8041564
39. [39]
  X. Li, J. Zhu, Eur. J. Org. Chem. 2016 (2016) 4724–4767. doi: 10.1002/ejoc.201600484
40. [40]
  J. Ghouilem, M.D. Robichon, F.L. Bideau, et al., Chem. Eur. J. 27 (2021) 491–511. doi: 10.1002/chem.202003267
41. [41]
  Q. Sun, H. Zhang, Q. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 19620–19625. doi: 10.1002/anie.202104430
42. [42]
  X. Gou, Y. Li, W. Shi, et al., Angew. Chem. Int. Ed. 61 (2022) e202205656. doi: 10.1002/anie.202205656
43. [43]
  N. Hussain, A. Hussain, RSC Adv. 11 (2021) 34369–34391. doi: 10.1039/D1RA06351K
44. [44]
  J. Liu, C. Lei, H. Gong, Sci. China Chem. 62 (2019) 1492–1496. doi: 10.1007/s11426-019-9501-4
45. [45]
  Y. Jiang, Q. Wang, X. Zhang, et al., Chem 7 (2021) 3377–3392. doi: 10.1016/j.chempr.2021.09.008
46. [46]
  Q. Wang, Q. Sun, Y. Jiang, et al., Nat. Synth. 1 (2022) 235–244. doi: 10.1038/s44160-022-00024-5
47. [47]
  Y. Ma, S. Liu, Y. Xi, et al., Chem. Commun. 55 (2019) 14657–14660. doi: 10.1039/C9CC07184A
48. [48]
  M. Li, Y.F. Qiu, C.T. Wang, et al., Org. Lett. 22 (2020) 6288–6293. doi: 10.1021/acs.orglett.0c02053
49. [49]
  W.Z. Shi, H. Li, G.C. Mu, et al., Org. Lett. 23 (2021) 2659–2663. doi: 10.1021/acs.orglett.1c00551
50. [50]
  M. Zhu, S. Messaoudi, ACS. Catal. 11 (2021) 6334–6342. doi: 10.1021/acscatal.1c01600
51. [51]
  W. Yao, G. Zhao, Y. Wu, et al., J. Am. Chem. Soc. 144 (2022) 3353–3359. doi: 10.1021/jacs.1c13299
52. [52]
  S.O. Badir, A. Dumoulin, J.K. Matsui, et al., Angew. Chem. Int. Ed. 57 (2018) 6610–6613. doi: 10.1002/anie.201800701
53. [53]
  A. Dumoulin, J.K. Matsui, Á. Gutiérrez-Bonet, et al., Angew. Chem. Int. Ed. 57 (2018) 6614–6618. doi: 10.1002/anie.201802282
54. [54]
  E.M. Miller, M.A. Walczak, Org. Lett. 23 (2021) 4289–4293. doi: 10.1021/acs.orglett.1c01035
55. [55]
  D. Takeda, M. Yoritate, H. Yasutomi, et al., Org. Lett. 23 (2021) 1940–1944. doi: 10.1021/acs.orglett.1c00402
56. [56]
  W. Shang, S.N. Su, R. Shi, et al., Angew. Chem. Int. Ed. 60 (2021) 385–390. doi: 10.1002/anie.202009828
57. [57]
  S. Xu, W. Zhang, C. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202218303. doi: 10.1002/anie.202218303
58. [58]
  H. Zeng, Y. Li, R. Wu, et al., Org. Lett. (2023), doi:10.1021/acs.orglett.3c00833. doi: 10.1021/acs.orglett.3c00833
59. [59]
  Y. Jiang, Y. Zhang, B.C. Lee, et al., Angew. Chem. Int. Ed. 62 (2023) e202305138. doi: 10.1002/anie.202305138
60. [60]
  L. Chen, Z. Zhao, S. Yu, Chin. Chem. Lett. 35 (2024) 109128. doi: 10.1016/j.cclet.2023.109128
61. [61]
  B. Liu, D. Liu, X. Rong, et al., Angew. Chem. Int. Ed. 62 (2023) e202218544. doi: 10.1002/anie.202218544
62. [62]
  M. Zeng, C. Yu, Y. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202300424. doi: 10.1002/anie.202300424
63. [63]
  J.R. Clark, K. Feng, A. Sookezian, et al., Nat. Chem. 10 (2018) 583–591. doi: 10.1038/s41557-018-0020-0
64. [64]
  P. Bhutani, G. Joshi, N. Raja, et al., J. Med. Chem. 64 (2021) 2339–2381. doi: 10.1021/acs.jmedchem.0c01786
65. [65]
  J. Panigot, W. Curley, J. Carb. Chem. 13 (1994) 293–302. doi: 10.1080/07328309408009194
66. [66]
  G. Díaz, A. Ponzinibbio, R.D. Bravo, Carb. Res. 393 (2014) 23–25. doi: 10.1016/j.carres.2014.04.009
67. [67]
  Z. Wang, H. Yin, G.C. Fu, Nature 563 (2018) 379–383. doi: 10.1038/s41586-018-0669-y
68. [68]
  D. Qian, S. Bera, X. Hu, J. Am. Chem. Soc. 143 (2021) 1959–1967. doi: 10.1021/jacs.0c11630
69. [69]
  F. Zhu, M.A. Walczak, J. Am. Chem. Soc. 142 (2020) 15127–15136. doi: 10.1021/jacs.0c06882
70. [70]
  Y. Wang, Y. He, S. Zhu, Acc. Chem. Res. 55 (2022) 3519–3536. doi: 10.1021/acs.accounts.2c00628
71. [71]
  S.J. He, J.W. Wang, Y. Li, et al., J. Am. Chem. Soc. 142 (2020) 214–221. doi: 10.1021/jacs.9b09415
72. [72]
  X.X. Wang, X. Lu, Y. Li, et al., Sci. China Chem. 63 (2020) 1586–1600. doi: 10.1007/s11426-020-9838-x
73. [73]
  Y. Li, W. Nie, Z. Chang, et al., Nat. Catal. 4 (2021) 901–911. doi: 10.1038/s41929-021-00688-w
74. [74]
  Y. Li, D. Liu, L. Wan, et al., J. Am. Chem. Soc. 144 (2022) 13961–13972. doi: 10.1021/jacs.2c06279
75. [75]
  S.Z. Sun, Y.M. Cai, D.L. Zhang, et al., J. Am. Chem. Soc. 144 (2022) 1130–1137. doi: 10.1021/jacs.1c12350
76. [76]
  X.X. Wang, Y.T. Xu, Z.L. Zhang, et al., Nat. Commun. 13 (2022) 1890. doi: 10.1038/s41467-022-29554-4
77. [77]
  J.W. Wang, Z. Li, D. Liu, et al., J. Am. Chem. Soc. 145 (2023) 10411–10421. doi: 10.1021/jacs.3c02950
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