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

Zhou Peng; Xu Zhaohui

doi:doi:10.11648/j.sd.20170507.18

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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

Zhou Peng, Xu Zhaohui

Published in Science Discovery (Volume 5, Issue 7)

Received: 28 December 2017 Accepted: 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), 2024. 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

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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

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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APA Style

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}
}

Copy | Download

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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