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  

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

作　　者：周鹏[1] 许祖俭[2] 许招会[3] HOU Peng;XU Zujian;XU Zhaohui(Energy and Enviroment Engineering Institute,Nanchang Institute of Technology,Nanchang 330044,China;Jiangxi Jishui Middle School,Jishui,Jiangxi 331600,China;Department of Chemistry and Chemical Engineering,Nanchang 330022,China)

机构地区：[1]南昌理工学院新能源与环境工程学院,南昌330044 [2]江西吉水中学,江西吉水331600 [3]江西师范大学化学化工学院,南昌330022

出　　处：《应用化学》2019年第5期509-514,共6页Chinese Journal of Applied Chemistry

基　　金：江西省教育厅科学技术研究项目(GJJ170170);江西省研究生创新基金(YC2015-B023)资助~~

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) Na OH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。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-Dglucose and acetyl bromide via acetylation and bromination. Then,five kinds of 4-formylphenyl(2,3,4,6-Otetraacetyl)-β-D-glucoside derivatives were obtained via glycosylation between intermediate 1 and4-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.

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 

分 类 号：O625.3[理学—有机化学]