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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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Authors
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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Abstract
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.
Keywords
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
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