Citation: Gefei Li, Yanlong Luo, Juan Mo, Masato Noguchi, Jie Jing, Zhenyang Luo, Shin-ichiro Shoda, Xin-Shan Ye. Hydrogen bond-assisted 1, 2-cis O-glycosylation under mild hydrogenolytic conditions[J]. Chinese Chemical Letters, ;2023, 34(4): 107754. doi: 10.1016/j.cclet.2022.107754 shu

Hydrogen bond-assisted 1, 2-cis O-glycosylation under mild hydrogenolytic conditions

Gefei Li ^{a, b, c} ,
Yanlong Luo ^a ,
Juan Mo ^b ,
Masato Noguchi ^c ,
Jie Jing ^a ,
Zhenyang Luo ^a ,
Shin-ichiro Shoda ^{c, *,} ,
Xin-Shan Ye ^{b, *,}

a.
College of Science, Nanjing Forestry University, Nanjing 210037, China
b.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
c.
Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan

shinichiro.shoda.a6@tohoku.ac.jp

xinshan@bjmu.edu.cn

Received Date: 17 June 2022
Revised Date: 10 August 2022
Accepted Date: 16 August 2022
Available Online: 18 August 2022

Figures(3)

A hydrogen bond-assisted α-selective glycosylation reaction by using 4, 6-dibenzyloxy-1, 3, 5-triazin-2-yl (DBT) β-glycosyl donors was developed for the efficient construction of 1, 2-cis-α-glycosidic bond in natural products. This method was applied successfully to the direct synthesis of complex oligosaccharide-derived glycolipids with simple protecting chemistry. Mechanistic studies using the NMR spectroscopy and DFT calculation provide a proof of concept for hydrogen bond-assisted glycosylation reaction towards α-specific construction of O-glycosidic linkage.
- O-Glycosylation,
- Hydrogen bond,
- α-Selectivity,
- Glycolipid,
- Natural product
1. [1]
  U. Mrudulakumari Vasudevan, E.Y. Lee, Biotechnol. Adv. 41 (2020) 107550–107572. doi: 10.1016/j.biotechadv.2020.107550
2. [2]
  Y. Yang, X. Zhang, B. Yu, Nat. Prod. Rep. 32 (2015) 1331–1355. doi: 10.1039/C5NP00033E
3. [3]
  B. Meng, Z. Zhu, D.C. Baker, Org. Biomol. Chem. 12 (2014) 5182–5191. doi: 10.1039/C4OB00626G
4. [4]
  S.S. Nigudkar, A.V. Demchenko, Chem. Sci. 6 (2015) 2687–2704. doi: 10.1039/C5SC00280J
5. [5]
  X. Qin, X.S. Ye, Chin. J. Chem. 39 (2021) 531–542. doi: 10.1002/cjoc.202000484
6. [6]
  W. Yong, X.S. Ye, Acta Chim. Sin. 77 (2019) 581–597. doi: 10.6023/A19040128
7. [7]
  T. Mukaiyama, Y. Murai, S. Shoda, Chem. Lett. 10 (1981) 431–432. doi: 10.1246/cl.1981.431
8. [8]
  J.P. Yasomanee, A.V. Demchenko, J. Am. Chem. Soc. 134 (2012) 20097–20102. doi: 10.1021/ja307355n
9. [9]
  A. Nakagawa, M. Tanaka, S. Hanamura, D. Takahashi, K. Toshima, Angew. Chem. Int. Ed. 54 (2015) 10935–10939. doi: 10.1002/anie.201504182
10. [10]
  M. Tanaka, A. Nakagawa, N. Nishi, et al., J. Am. Chem. Soc. 140 (2018) 3644–3651. doi: 10.1021/jacs.7b12108
11. [11]
  S. Izumi, Y. Kobayashi, Y. Takemoto, Org. Lett. 21 (2019) 665–670. doi: 10.1021/acs.orglett.8b03823
12. [12]
  S. Tomita, M. Tanaka, M. Inoue, et al., J. Org. Chem. 85 (2020) 16254–16262. doi: 10.1021/acs.joc.0c02093
13. [13]
  R.A. Mensink, T.J. Boltje, Chem. Eur. J. 23 (2017) 17637–17653. doi: 10.1002/chem.201700908
14. [14]
  M. Shadrick, Y. Singh, A.V. Demchenko, J. Org. Chem. 85 (2020) 15936–15944. doi: 10.1021/acs.joc.0c01279
15. [15]
  Y. Zhang, Z. Chen, Y. Huang, et al., Angew. Chem. Int. Ed. 59 (2020) 7576–7584. doi: 10.1002/anie.202000992
16. [16]
  Y. Zhang, H. He, Z. Chen, et al., Angew. Chem. Int. Ed. 60 (2021) 12597–12606. doi: 10.1002/anie.202103826
17. [17]
  X. Liu, Y. Song, A. Liu, et al., Angew. Chem. Int. Ed. 61 (2022) e202201510.
18. [18]
  F. Yu, J. Li, P.M. DeMent, et al., Angew. Chem. Int. Ed. 58 (2019) 6957–6961. doi: 10.1002/anie.201901346
19. [19]
  S.J. Moons, R.A. Mensink, J.P.J. Bruekers, et al., J. Org. Chem. 84 (2019) 4486–4500. doi: 10.1021/acs.joc.9b00022
20. [20]
  J.C. Hu, A.W. Feng, B.Y. Chang, C.H. Lin, K.T. Mong, Org. Biomol. Chem. 15 (2017) 5345–5356. doi: 10.1039/C7OB00839B
21. [21]
  D.K. Njeri, C.J. Pertuit, J.R. Ragains, Org. Biomol. Chem. 18 (2020) 2405–2409. doi: 10.1039/D0OB00373E
22. [22]
  D.K. Njeri, E.A. Valenzuela, J.R. Ragains, Org. Lett. 23 (2021) 8214–8218. doi: 10.1021/acs.orglett.1c02947
23. [23]
  Z. Zheng, L. Zhang, Carbohydr. Res. 471 (2019) 56–63. doi: 10.1016/j.carres.2018.10.010
24. [24]
  C. Zhang, H. Zuo, G.Y. Lee, et al., Nat. Chem. 14 (2022) 684–694.
25. [25]
  M. Liu, K.M. Liu, D.C. Xiong, et al., Angew. Chem. Int. Ed. 59 (2020) 15204–15208. doi: 10.1002/anie.202006115
26. [26]
  K.M. Liu, P.Y. Wang, Z.Y. Guo, et al., Angew. Chem. Int. Ed. 61 (2022) e202114726.
27. [27]
  M. Ishihara, Y. Takagi, G. Li, M. Noguchi, S. Shoda, Chem. Lett. 42 (2013) 1235–1237. doi: 10.1246/cl.130646
28. [28]
  T. Ikawa, K. Hattori, H. Sajiki, K. Hirota, Tetrahedron 60 (2004) 6901–6911. doi: 10.1016/j.tet.2004.05.098
29. [29]
  Y. Geng, A. Kumar, H.M. Faidallah, et al., Angew. Chem. Int. Ed. 52 (2013) 10089–10092. doi: 10.1002/anie.201302158
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