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

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。

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

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.