Citation: Yingle Feng, Jie Yang, Chenglin Cai, Taotao Sun, Qi Zhang, Yonghai Chai. Catalytic and highly stereoselective β-mannopyranosylation using a 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate as donor[J]. Chinese Chemical Letters, ;2022, 33(11): 4878-4881. doi: 10.1016/j.cclet.2022.02.071 shu

Catalytic and highly stereoselective β-mannopyranosylation using a 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate as donor

Yingle Feng ^{a, *,} ,
Jie Yang ^a ,
Chenglin Cai ^a ,
Taotao Sun ^a ,
Qi Zhang ^b ,
Yonghai Chai ^{a, *,}

a.
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China
b.
School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China

fengyingle@snnu.edu.cn

ychai@snnu.edu.cn

Received Date: 24 November 2021
Revised Date: 21 February 2022
Accepted Date: 25 February 2022
Available Online: 1 March 2022

Figures(2)

An efficient and catalytic protocol for highly stereoselective construction of β-mannopyranosylation has been developed. Glycosylation of 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate with various acceptors proceeded smoothly in the presence of 5% Hg(Ⅱ) at room temperature, resulting in the corresponding β-mannosides in high yield and exclusive β-stereoselectivity.
- β-Mannanoside,
- 2,6-Lactone,
- Catalytic glycosylation,
- Ortho-hexynylbenzoates,
- 1,2-cis Glycosylation
1. [1]
  K. Sasaki, K. Tohda, Tetrahedron Lett. 59 (2018) 496–503. doi: 10.1016/j.tetlet.2017.12.077
2. [2]
  S.S. Nigudkar, A.V. Demchenko, Chem. Sci. 6 (2015) 2687–2704. doi: 10.1039/C5SC00280J
3. [3]
  G. Stork, G. Kim, J. Am. Chem. Soc. 114 (1992) 1087–1088. doi: 10.1021/ja00029a047
4. [4]
  A.A.H. Abdel-Rahman, E.S.H. El Ashry, R.R. Schmidt, Carbohydr. Res. 337 (2002) 195–206. doi: 10.1016/S0008-6215(01)00306-8
5. [5]
  F. Ding, A. Ishiwata, Y. Ito, Org. Lett. 20 (2018) 4833–4837. doi: 10.1021/acs.orglett.8b01979
6. [6]
  S.G. Pistorio, J.P. Yasomanee, A.V. Demchenko, Org. Lett. 16 (2014) 716–719. doi: 10.1021/ol403396j
7. [7]
  P. Sun, P. Wang, Y. Zhang, et al., J. Org. Chem. 80 (2015) 4164–4175. doi: 10.1021/acs.joc.5b00140
8. [8]
  A. Gucchait, A.K. Misra, Org. Biomol. Chem. 17 (2019) 4605–4610. doi: 10.1039/C9OB00670B
9. [9]
  Y. Zhu, B. Yu, Chem. Eur. J. 21 (2015) 8771–8780. doi: 10.1002/chem.201500648
10. [10]
  M. Heuckendorff, J. Bendix, C.M. Pedersen, M. Bols, Org. Lett. 16 (2014) 1116–1119. doi: 10.1021/ol403722f
11. [11]
  D. Crich, S. Sun, J. Org. Chem. 61 (1996) 4506–4507. doi: 10.1021/jo9606517
12. [12]
  L.J. van den Bos, J. Dinkelaar, H.S. Overkleeft, G.A. van der Marel, J. Am. Chem. Soc. 128 (2006) 13066–13067. doi: 10.1021/ja064787q
13. [13]
  Y. Hashimoto, S. Tanikawa, R. Saito, K. Sasaki, J. Am. Chem. Soc. 138 (2016) 14840–14843. doi: 10.1021/jacs.6b08874
14. [14]
  H. Xu, L. Chen, Q. Zhang, et al., Chem. Asian J. 14 (2019) 1424–1428. doi: 10.1002/asia.201801740
15. [15]
  H. Elferink, R.A. Mensink, P.B. White, T.J. Boltje, Angew. Chem. Int. Ed. 55 (2016) 11217–11220. doi: 10.1002/anie.201604358
16. [16]
  M. Tanaka, J. Nashida, D. Takahashi, K. Toshima, Org. Lett. 18 (2016) 2288–2291. doi: 10.1021/acs.orglett.6b00926
17. [17]
  N. Nishi, J. Nashida, E. Kaji, D. Takahashi, K. Toshima, Chem. Commun. 53 (2017) 3018–3021. doi: 10.1039/C7CC00269F
18. [18]
  G. Hodosi, P. Kováč, J. Am. Chem. Soc. 119 (1997) 2335–2336. doi: 10.1021/ja964021y
19. [19]
  H. Nguyen, D. Zhu, X. Li, J. Zhu, Angew. Chem. Int. Ed. 55 (2016) 4767–4771. doi: 10.1002/anie.201600488
20. [20]
  K. Ohara, C.C. Lin, P.J. Yang, et al., J. Org. Chem. 78 (2013) 6390–6411. doi: 10.1021/jo4005266
21. [21]
  D. Crich, A. Banerjee, Q. Yao, J. Am. Chem. Soc. 126 (2004) 14930–14934. doi: 10.1021/ja047194t
22. [22]
  S.L. Tang, N.L. Pohl, Org. Lett. 17 (2015) 2642–2645. doi: 10.1021/acs.orglett.5b01013
23. [23]
  M.T. Walvoort, H. van den Elst, O.J. Plante, et al., Angew. Chem. Int. Ed. 51 (2012) 4393–4396. doi: 10.1002/anie.201108744
24. [24]
  D. Pan, L. Zhang, Q. Hua, Y. Yang, Org. Biomol. Chem. 17 (2019) 6174–6177. doi: 10.1039/C9OB01254K
25. [25]
  H. Imagawa, A. Kinoshita, T. Fukuyama, H. Yamamoto, M. Nishizawa, Tetrahedron Lett. 47 (2006) 4729–4731. doi: 10.1016/j.tetlet.2006.04.114
26. [26]
  Y. Li, Y. Yang, B. Yu, Tetrahedron Lett. 49 (2008) 3604–3608. doi: 10.1016/j.tetlet.2008.04.017
27. [27]
  W. Li, B. Yu, Chem. Soc. Rev. 47 (2018) 7954–7984. doi: 10.1039/C8CS00209F
28. [28]
  Z. Lu, T. Li, S.R. Mudshinge, B. Xu, G.B. Hammond, Chem. Rev. 121 (2021) 8452–8477. doi: 10.1021/acs.chemrev.0c00713
29. [29]
  Y. Zu, C. Cai, J. Sheng, et al., Org. Lett. 21 (2019) 8270–8274. doi: 10.1021/acs.orglett.9b03038
30. [30]
  M. Yamabhai, S. Sak-Ubol, W. Srila, D. Haltrich, Crit. Rev. Biotechnol. 36 (2016) 32–42. doi: 10.3109/07388551.2014.923372
31. [31]
  S. van der Vorm, T. Hansen, J.M.A. van Hengst, et al., Chem. Soc. Rev. 48 (2019) 4688–4706. doi: 10.1039/C8CS00369F
32. [32]
  C.W. Chang, M.H. Lin, C.K. Chan, et al., Angew. Chem. Int. Ed. 60 (2021) 12413–12423. doi: 10.1002/anie.202013909
33. [33]
  N. Shibata, Y. Okawa, Chem. Pharm. Bull. 58 (2010) 1386–1390. doi: 10.1248/cpb.58.1386
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