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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

Received: 28 December 2017     Published: 28 December 2017
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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.

Published in Science Discovery (Volume 5, Issue 7)
DOI 10.11648/j.sd.20170507.18
Page(s) 519-523
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2017. Published by Science Publishing Group

Keywords

N-methylimidazole Trifluoromethyl Sulfonate, 2,2-dimethyl-1,3-dioxane-4,6-dione, Knoevenagel Condensation Reaction, 4-formylphenyl-β-D-glucoside

References
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    Zhou Peng, Xu Zhaohui. (2017). 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, 5(7), 519-523. https://doi.org/10.11648/j.sd.20170507.18

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    ACS Style

    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. Sci. Discov. 2017, 5(7), 519-523. doi: 10.11648/j.sd.20170507.18

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    AMA Style

    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. Sci Discov. 2017;5(7):519-523. doi: 10.11648/j.sd.20170507.18

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  • @article{10.11648/j.sd.20170507.18,
      author = {Zhou Peng and Xu Zhaohui},
      title = {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},
      journal = {Science Discovery},
      volume = {5},
      number = {7},
      pages = {519-523},
      doi = {10.11648/j.sd.20170507.18},
      url = {https://doi.org/10.11648/j.sd.20170507.18},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sd.20170507.18},
      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.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - 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
    AU  - Zhou Peng
    AU  - Xu Zhaohui
    Y1  - 2017/12/28
    PY  - 2017
    N1  - https://doi.org/10.11648/j.sd.20170507.18
    DO  - 10.11648/j.sd.20170507.18
    T2  - Science Discovery
    JF  - Science Discovery
    JO  - Science Discovery
    SP  - 519
    EP  - 523
    PB  - Science Publishing Group
    SN  - 2331-0650
    UR  - https://doi.org/10.11648/j.sd.20170507.18
    AB  - 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.
    VL  - 5
    IS  - 7
    ER  - 

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Author Information
  • Energy and Environment Engineering Institute, Nanchang Institute of Technology, Nanchang, China

  • Chemistry and Chemical Engineering Department, Jiangxi Normal University, Nanchang, China

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