Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (5): 509-514.DOI: 10.11944/j.issn.1000-0518.2019.05.180331

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

ZHOU Penga,XU Zujianb,XU Zhaohuic*()   

  1. aEnergy and Enviroment Engineering Institute,Nanchang Institute of Technology,Nanchang 330044,China
    bJiangxi Jishui Middle School,Jishui,Jiangxi 331600,China
    cDepartment of Chemistry and Chemical Engineering,Nanchang 330022,China
  • Received:2018-10-15 Accepted:2018-12-24 Published:2019-05-01 Online:2019-05-06
  • Contact: XU Zhaohui
  • Supported by:
    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)


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.

Key words: 4-hydroxybenzaldhyde, tris(3,6-dioxaheptyl)amine(TDA-1), glycosylation, 4-formylphenyl-β-D-glucoside;