SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 6: 1694 - 1705

DOI: https://doi.org/10.6023/cjoc202202002

ARTICLES

Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides

  • Mengnan Lai ,
  • Qiuyuan Wang ,
  • Min Hua ,
  • Nianyu Huang ,
  • Hui Yao
Expand
  • Key Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002
† These authors contributed equally to this work
*E-mail: ;

Received date: 2022-02-04

  Revised date: 2022-02-23

  Online published: 2022-03-22

Supported by

Programme of Introducing Talents of Discipline to Universities(111 Project); Programme of Introducing Talents of Discipline to Universities(D20015); Natural Science Foundation of Hubei Province(2020CFB205); Educational Commission of Hubei Province(Q20201204); Dissertation Training Fund of China Three Gorges University(2021SSPY158)

Fold

Abstract

An open-air stereoselective preparation of C-aryl fucosides and arabinosides was reported using 3,4-O-carbonate glycals and arylboronicic acids based on a palladium-catalyzed decarboxylative allylation at ambient conditions and the configurations of products were determined by NMR, HRMS and X-ray single crystal diffraction analysis. Competitive reactions indicated that this approach has good compatibility with amino and alcoholic/phenolic hydroxyl groups. Further functionlization of unsaturated C-glycosides can be used to prepare a variety of C-glycosides. This mild method is simple in operation, wide application in substrate range, which provides a new idea for the rapid construction of carbohydrate library.

Key words： 3,4-O-carbonate glycal; stereoselectivity; C-fucoside; C-arabinoside; C-glycosylation

Cite this article

Mengnan Lai , Qiuyuan Wang , Min Hua , Nianyu Huang , Hui Yao . Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1694 -1705 . DOI: 10.6023/cjoc202202002

References

[1]
(a) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
[1]
(b) Varki, A. Glycobiology 2017, 27, 3.
[1]
(c) Zhang, Y. Q.; Chen, Z. X.; Huang, Y. Y.; He, S. J.; Yang, X. K.; Wu, Z. B.; Wang, X. F.; Xiao, G. Z. Angew. Chem., Int. Ed. 2020, 59, 7576.
[2]
Li, F.-F.; Qu, J. Chin. J. Org. Chem. 2021, 41, 3948. (in Chinese)
[2]
( 李非凡, 渠瑾, 有机化学, 2021, 40, 3948.)
[3]
(a) Wang, Q. B.; Duan, J.; Tang, P. P.; Chen, G.; He, G. Sci. China: Chem. 2020, 63, 1613.
[3]
(b) An, Y.; Zhang, B. S.; Ding, Y. N.; Zhang, Z.; Gou, X. Y.; Li, X. S.; Wang, X.; Li, Y.; Liang, Y. M. Chem. Sci. 2021, 12, 13144.
[4]
Wang, Y.-S.; Wang, S.; Zhang, H.-L.; Li, C.-W. Chin. Agric. Sci. Bull. 2019, 35, 127. (in Chinese)
[4]
( 王永胜, 王硕, 张慧林, 李冲伟, 中国农学通报, 2019, 35, 127.)
[5]
Conti, F.; Dall'Agata, M.; Gramenzi, A.; Biselli, M. Biomark. Med. 2015, 9, 1343.
[6]
Cazarolli, L. H.; Kappel, V. D.; Pereira, D. F.; Moresco, H. H.; Brighente, I. M.; Pizzolatti, M. G.; Silva, F. R. Fitoterapia 2012, 83, 1176.
[7]
Yu, J.-X. Ph.D. Dissertation, Peking University Health Science Center, Beijing, 1992. (in Chinese)
[7]
( 郁建兴, 博士论文, 北京医科大学, 北京, 1992.)
[8]
Qin, Y. M.S. Thesis, Fudan University, Shanghai, 2014. (in Chinese)
[8]
( 秦艳, 硕士论文, 复旦大学, 上海, 2014.)
[9]
Xie, C.; Veitch, N. C.; Houghton, P. J.; Simmonds, M S. J. Chem. Pharm. Bull. 2003, 51, 1204.
[10]
Tang, S.-B. Ph.D. Dissertation, Tianjin University, Tianjin, 2016. (in Chinese)
[10]
( 唐生表, 博士论文, 天津大学, 天津, 2016.)
[11]
Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013.
[12]
Guo, Z.-Y.; Bai, J.-H.; Liu, M.; Xiong, D.-C.; Ye, X.-S. Chin. J. Org. Chem. 2020, 40, 3094. (in Chinese)
[12]
( 郭真言, 柏金和, 刘苗, 熊德彩, 叶新山, 有机化学, 2020, 40, 3094.)
[13]
Xiang, S. H.; Cai, S.; Zeng, J.; Liu, X. W. Org. Lett. 2011, 13, 4608.
[14]
Lai, M. N.; Othman, K. A.; Yao, H.; Wang, Q. Y.; Feng, Y. K.; Huang, N. Y.; Liu, M. G.; Zou, K. Org. Lett. 2020, 22, 1144.
[15]
Musawir, M.; Davey, P. N.; Kelly, G.; Kozhevnikov, I. V. Chem. Commun. 2003, 1414.
[16]
Kim, H.; Men, H. B.; Lee, C. J. Am. Chem. Soc. 2004, 126, 1336.
[17]
Yan, X. X.; Feng, F.; Zhou, L.; Chen, L. R.; Tang, S. C.; Liu, J.; Cai, F.; Wang, X. L. Sci. China. Chem. 2021, 64, 552.
[18]
(a) Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
[18]
(b) Ohmiya, H.; Makida, Y.; Tanaka, T.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 17276.
[19]
(a) Yao, H.; Zhang, S. S.; Leng, W. L.; Leow, M. L.; Xiang, S.; He, J.; Liao, H.; Le Mai Hoang, K.; Liu, X. W. ACS Catal. 2017, 7, 5456.
[19]
(b) Wang, Y.; Yao, H.; Hua, M.; Jiao, Y.; He, H. B.; Liu, M. G.; Huang, N. Y.; Zou, K. J. Org. Chem. 2020, 85, 7485.
[19]
(c) Liu, Y. X.; Jiao, Y.; Luo, H. J.; Huang, N. Y.; Lai, M. N.; Zou, K.; Yao, H. ACS Catal. 2021, 11, 5287.
Options
Outlines

/

〈 〉