Citation: ZHOU Peng, XU Zujian, XU Zhaohui. Efficent Synthesis of 4-Formylphenyl(2, 3, 4, 6-O-tetraacetyl)-β-D-glucoside Derivatives[J]. Chinese Journal of Applied Chemistry, ;2019, 36(5): 509-514. doi: 10.11944/j.issn.1000-0518.2019.05.180331 shu

Efficent Synthesis of 4-Formylphenyl(2, 3, 4, 6-O-tetraacetyl)-β-D-glucoside Derivatives

ZHOU Peng ^a ,
XU Zujian ^b ,
XU Zhaohui ^c,,

a.
Energy and Enviroment Engineering Institute, Nanchang Institute of Technology, Nanchang 330044, China
b.
Jiangxi Jishui Middle School, Jishui, Jiangxi 331600, China
c.
Department of Chemistry and Chemical Engineering, Nanchang 330022, China

Corresponding author: XU Zhaohui, gotoxzh@163.com
Received Date: 15 October 2018
Revised Date: 19 November 2018
Accepted Date: 24 December 2018

Fund Project: Supported by the Science and Technology Research Project of Jiangxi Provincial Education Department (No.GJJ170170) and the Graduate Innovation Fundation of Jiangxi Province (No.YC2015-B023)the Science and Technology Research Project of Jiangxi Provincial Education Department GJJ170170the Graduate Innovation Fundation of Jiangxi Province YC2015-B023

Figures(1)

In order to overcome the low yield, long reaction time, and the difficult product separation in current methods, 2, 3, 4, 6-O-tetraacetyl-α-D-glucopyranosyl bromide(1) was firstly prepared from β-D-glucose and acetyl bromide via acetylation and bromination. Then, five kinds of 4-formylphenyl(2, 3, 4, 6-O-tetraacetyl)-β-D-glucoside derivatives were obtained via glycosylation between intermediate 1 and 4-hydroxybenzaldhyde derivatives. The yields of products reached 61%~69% when 10%(mass fraction) NaOH solution and tris(3, 6-dioxaheptyl)amine(TDA-1) were used as base and phase transfer catalyst, respectively. The obtained compounds were confirmed by nuclear magnetic resonance(NMR). This method shows advantages in high yield, mild conditions and simple operation.
- 4-hydroxybenzaldhyde,
- tris(3, 6-dioxaheptyl)amine(TDA-1),
- glycosylation,
- 4-formylphenyl-β-D-glucoside
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