4-甲酰基苯基(2,3,4,6-O-四乙酰基)-β-D-葡萄糖苷衍生物的有效合成

doi:10.11944/j.issn.1000-0518.2019.05.180331

摘要/Abstract

摘要：

为克服目前合成方法存在收率较低,反应时间长、产品分离困难等不足,本文以β-D-葡萄糖、乙酰溴为原料,经乙酰化、溴代反应合成了糖基体2,3,4,6-O-四乙酰基-α-D-溴代葡萄糖,再与4-羟基苯甲醛衍生物经糖苷化反应合成了5种4-甲酰基苯基(2,3,4,6-O-四乙酰基)-β-D-葡萄糖苷衍生物。在合成4-甲酰基苯基(2,3,4,6-O-四乙酰基)-β-D-葡萄糖苷衍生物的过程中,采用10%(质量分数)NaOH溶液为缚酸剂,三(3,6-二氧杂庚基)胺(TDA-1)为相转移催化剂,反应物的收率为61%~69%,并应用核磁共振技术确定了产品的结构。该方法具有产品收率较高,反应温和、操作简单等优点。

关键词: 4-羟基苯甲醛, 三(3,6-二氧杂庚基)胺, 糖苷化, 4-甲酰基苯基-β-D-葡萄糖苷;

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;

周鹏,许祖俭,许招会. 4-甲酰基苯基(2,3,4,6-O-四乙酰基)-β-D-葡萄糖苷衍生物的有效合成[J]. 应用化学, 2019, 36(5): 509-514.

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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