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

doi:10.11944/j.issn.1000-0518.2019.05.180331

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 Peng^a,XU Zujian^b,XU Zhaohui^c^*()

^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)

Abstract

Abstract:

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;

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.

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

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