Efficent Synthesis of 5-(4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl))benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives
Science Discovery
Volume 5, Issue 7, December 2017, Pages: 519-523
Received: Dec. 28, 2017; Published: Dec. 28, 2017
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Zhou Peng, Energy and Environment Engineering Institute, Nanchang Institute of Technology, Nanchang, China
Xu Zhaohui, Chemistry and Chemical Engineering Department, Jiangxi Normal University, Nanchang, China
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Objective Synthesis of gastrodin intermediate 4-formylphenyl(2,3,4,6-O-tetraacetyl)-β-D-glucoside analogues. Methods 5-(4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)) benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives were synthesized by the Knoevenagel reaction of self-made 4-formylphenyl(2,3,4,6-O-tetraacetyl)-β-D-glucoside and 2,2-dimethyl-1,3-dioxane -4,6-dione in the presence of N-methylimidazole trifluoromethyl sulfonate. Results and conclusions five products of gastrodin intermediate analogues characterized by NMR and MS(ESI). The reaction has the advantages of high yields(76%~84%), mild conditions, simple operation and environmental friendliness. N-methylimidazole trifluoromethyl sulfonate could be recycled and reused several times without significant loss of its efficiency.
N-methylimidazole Trifluoromethyl Sulfonate, 2,2-dimethyl-1,3-dioxane-4,6-dione, Knoevenagel Condensation Reaction, 4-formylphenyl-β-D-glucoside
To cite this article
Zhou Peng, Xu Zhaohui, Efficent Synthesis of 5-(4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl))benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives, Science Discovery. Vol. 5, No. 7, 2017, pp. 519-523. doi: 10.11648/j.sd.20170507.18
Zhao, J. P.; Pan, W. X.; Chen, W. X. Nat. Prod. Res. Dev. 1992, 4, 35(in Chinese).
Wang, Y. Y.; Tian, L. Y.; Yang, Y.; Sun, W. Y.; Wang, W. Acta Pharmac. Sin. 2017, 52, 378(in Chinese).
Zhu, Q. L.; Li, Y.; Li, J.; Tang, Q.; Guo, C. H.; Yi, S. F. West China J. Pharm. Sci. 2008, 23, 12 (in Chinese).
Bai, Y. F.; Yin, H.; Bi, H. P.; Zhang, Y. B.; Liu, T., Ma, Y. H. Metab. Eng. 2016, 35, 138.
Liu, H. -M.; Liu, H. -L.; Yuan, Y. -J.; Tang, X. R.; Ji, S. J. Chin. J. Org. Chem. 2003, 23, 1159(in Chinese).
Bruns, R.; Wernicke, A.; Koll, P. Tetrahedron, 1999, 55, 9793.
Huang, Z. -Z.; Wu, L. -L.; Huang, X. Chin. J. Org. Chem. 2000, 20, 88(in Chinese).
Abdallah-EI, A. S.; Texier-Boullet, F.; Hamelin, J. Synthesis 1994, 26, 258.
Shital, S.; Gajanan, R.; Arjun, K.; Santosh, K.; Rajashri, S. Helv. Chim. Acta, 2011, 94, 1943.
Chakrabarty, M.; Mukherjee, R.; Chakrabarty, M.; Arima, S.; Harigaya, Y. Lett. Org. Chem. 2006, 3, 868.
Xu, Z. -H.; Lin, C. -H. Chin. J. Org. Chem. 2013, 33, 1154(in Chinese).
Shi, D. -Q.; Ni, S. -N.; Dou, G. -L. Chin. J. Org. Chem. 2009, 29, 788(in Chinese).
Peter, W.; Wilhelm, K. Angew. Chem., Int. Ed. 2000, 39, 3772.
Plechkova, N.-V.; Seddon, K.-R. Chem. Soc. Rev. 2008, 370, 123.
Liu, N. –N.; Chen, X.; Zhang, Q. –S.; Wu, Q. P. Chin. J. Org. Chem. 2014, 34, 1364(in Chinese).
Wen, H.; Lin, C. L.; Que, L.; Ge, H.; Ma, L.; Wan, H. Q; Pen, W. L.; Wang, Z. H.; Song, H. C. Eur. J. Med. Chem. 2008, 43, 166.
Lars, K.; Joachim, T. J. Carbohyd. Chem. 2003, 22, 9.
Xu, Z. H.; Zhang, H. F.; Xiong, Y. K.; Liu, D. Y.; Huang, Q. S. Heterocycles, 2016, 92, 2252.
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