廉价钴催化下β-D-葡萄烯糖硫苷的立体选择性合成
收稿日期: 2022-02-18
修回日期: 2022-03-23
网络出版日期: 2022-04-15
基金资助
国家自然科学基金(82003621); 湖北省自然科学基金(2020CFB205); 湖北省教育厅自然科学基金(Q20201204)
Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides
Received date: 2022-02-18
Revised date: 2022-03-23
Online published: 2022-04-15
Supported by
National Natural Science Foundation of China(82003621); Natural Science Foundation of Hubei Province(2020CFB205); Natural Science Foundation of the Educational Commission of Hubei Province(Q20201204)
华敏 , 孙阳星 , 张雪晴 , 姚辉 , 黄年玉 . 廉价钴催化下β-D-葡萄烯糖硫苷的立体选择性合成[J]. 有机化学, 2022 , 42(7) : 2140 -2154 . DOI: 10.6023/cjoc202202021
A method of stereoselective synthesis of β-D-thioglycosides from glucosyl-3-pyridinate donor and thiophenols/ thiols catalyzed by Co(BF4)2 was reported. The chemical structures of the target compounds were confirmed by nuclear magnetic resonance, high-resolution mass spectrometry and single crystal X-ray diffraction. The reaction has good functional group compatibility with all kinds of mercaptans and thiophenols, and can tolerate active sulfur nucleophiles including ester group, phenol/alcohol hydroxyl group, amino group and acetylamino group. It can also be used for the efficient synthesis of thioglycopeptides, which provides a new way for the rapid preparation of thioglycosides.
Key words： Co-catalysis; glycosylation reaction; thioglycoside; glycopeptide; synthesis
| [1] | (a) Turganbay, S.; Aidarova, S. B.; Bekturganova, N. E.; Li, C. S.; Musabekov, K. B.; Kumargalieva, S. S.; Toshtay, K. Eurasian Chem.-Technol. J. 2012, 14, 313.? |
| [1] | (b) Jacob, C. Nat. Prod. Rep. 2006, 23, 851. |
| [1] | (c) Devendar, P.; Yang, G. F. Top. Curr. Chem. 2017, 375, 82. |
| [1] | (d) Crockett, M. P.; Evans, A. M.; Worthington, M. J.; Albuquerque, I. S.; Slattery, A. D.; Gibson, C. T.; Campbell, J. A.; Lewis, D. A.; Bernardes, G. J.; Chalker, J. M. Angew. Chem., Int. Ed. 2016, 55, 1714. |
| [1] | (e) Wang, M.; Wang, C. H.; Jiang, X. F. Chin. J. Org. Chem. 2019, 39, 2139. (in Chinese) |
| [1] | ( 王明, 王翠红, 姜雪峰, 有机化学, 2019, 39, 2139.) |
| [2] | (a) Driguez, H. ChemBioChem 2001, 2, 311. |
| [2] | (b) Agrawal, S.; Wozniak, M.; Luc, M.; Walaszek, K.; Pielka, E.; Szeja, W.; Gamian, A.; Ziolkowski, P. Oncotarget 2017, 8, 114173. |
| [2] | (c) Zhu, X.; Stolz, F.; Schmidt, R. R. J. Org. Chem. 2004, 69, 7367. |
| [3] | (a) Witczak, Z. J. Curr. Med. Chem. 1999, 6, 165. |
| [3] | (b) Witczak, Z. J.; Culhane, J. M. Appl. Microbiol. Biotechnol. 2005, 69, 237. |
| [4] | (a) Wang, H.; Zhu, X. Org. Biomol. Chem. 2014, 12, 7119. |
| [4] | (b) Zeng, X.; Smith, R.; Zhu, X. J. Org. Chem. 2013, 78, 4165. |
| [4] | (c) Gamblin, D. P.; Scanlan, E. M.; Davis, B. G. Chem. Rev. 2009, 109, 131. |
| [5] | (a) Wu, B.; Yang, X.; Yan, M. J. Med. Chem. 2019, 62, 7751. |
| [5] | (b) Tota, A.; Carlucci, C.; Pisano, L.; Cutolo, G.; Clarkson, G. J.; Romanazzi, G.; Luisi, R. Org. Biomol. Chem. 2020, 18, 3893. |
| [5] | (c) Hutton, M. L.; Pehlivanoglu, H.; Vidor, C. J.; James, M. L.; Thomson, M. J.; Lyras, D. J. Antimicrob. Chemother. 2020, 75, 409. |
| [5] | (d) Umemura, E.; Wakiyama, Y.; Kumura, K.; Ueda, K.; Masaki, S.; Watanabe, T.; Yamamoto, M.; Hirai, Y.; Ajito, K. S. J. Antibiot. 2013, 66, 195. |
| [5] | (e) Del-Rosso, J. Q.; Schmidt, N. F. Cutis 2010, 85, 15. |
| [6] | (a) Yadav, J. S.; Reddy, B. S.; Bhasker, E. V.; Raghavendra, S.; Narsaiah, A. V. Tetrahedron Lett. 2017, 48, 677. |
| [6] | (b) Li, X.; Zhu, J. Eur. J. Org. Chem. 2016, 2016, 4724. |
| [6] | (c) Liu, Q. F.; Zhang, G. S. Chin. J. Org. Chem. 2009, 12, 1890. (in Chinese) |
| [6] | 刘青峰, 张贵生, 有机化学, 2009, 12, 1890.) |
| [7] | (a) Yadav, J. S.; Reddy, B. V. S.; Geetha, V. Synth. Commun. 2003, 33, 717. |
| [7] | (b) Tian, Q.; Zhu, X. M.; Yang, J. S. Synth. Commun. 2007, 37, 691. |
| [7] | (c) Babu, J.; Khare, A.; Vankar, Y. Molecules 2005, 10, 884. |
| [8] | (a) Liu, Y.; Song, T.; Meng, W.; Xu, Y.; Wang, P. G.; Zhao, W. Tetrahedron Lett. 2016, 57, 2758. |
| [8] | (b) Xiang, S.; He, J.; Tan, Y. J.; Liu, X. W. Angew. Chem., Int. Ed. 2015, 54, 604. |
| [8] | (c) Liu, Y.; Jiao, Y.; Luo, H.; Huang, N.; Lai, M.; Zou, K.; Yao, H. ACS Catal. 2021, 11, 5287. |
| [9] | (a) McKay, M. J.; Nguyen, H. M. ACS Catal. 2012, 2, 1563. |
| [9] | (b) Liao, H.; Ma, J.; Yao, H.; Liu, X. W. Org. Biomol. Chem. 2018, 16, 1791. |
| [10] | (a) Liu, X.; Lin, Y.; Liu, A.; Sun, Q.; Sun, H.; Xu, P.; Li, W. Chin. J. Chem. 2022, 40, 443. |
| [10] | (b) Dziuba, K.; Lubańska, M.; Pietrusiewicz, K. M. Synthesis 2020, 52, 909. |
| [10] | (c) Bedford, R. B.; Cazin, C. S. Chem. Commun. 2001, 17, 1540. |
| [10] | (d) Fleckenstein, C. A.; Plenio, H. Chem.-Eur. J. 2008, 14, 4267. |
| [11] | (a) Gómez, A. M.; Lobo, F.; Uriel, C.; López, J. C. Eur. J. Org. Chem. 2013, 2013, 7221. |
| [11] | (b) Gómez, A. M.; Miranda, S.; López, J. C. Carbohydr. Chem. 2016, 42, 210. |
| [11] | (c) Minbiole, E. C.; Minbiole, K. P. J. Antibiot. 2016, 69, 213. |
| [12] | (a) Xiang, S.; Lu, Z.; He, J.; Zeng, J.; Liu, X. W. Chem.-Eur. J. 2013, 19, 14047. |
| [12] | (b) Ji, L.; Xiang, S. H.; Leng, W. L.; Liu, X. W. Org. Lett. 2015, 17, 1357. |
| [13] | Kim, H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 1336. |
| [14] | (a) Sun, M.; Chen, J. F.; Chen, S.; Li, C. Org. Lett. 2019, 21, 1278. |
| [14] | (b) Ghorai, S.; Chirke, S. S.; Xu, W. B.; Chen, J. F.; Li, C. J. Am. Chem. Soc. 2019, 141, 11430. |
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