摘要
核糖及其衍生物是抗病毒药物的重要基团,但是目前本科生实验教学实践中尚未见核糖选择性保护的案例。本文采用核糖与丙酮和苯甲醇在酸催化下“一锅”完成核糖1-位糖苷化和2,3-位缩丙酮化反应,实现呋喃型核糖羟基的选择性保护。该实验原料易得、条件温和、重复性好,反应过程中涉及减压蒸馏、萃取、重结晶、过滤等基础操作,非常适合锻炼学生的有机化学综合实验技能。实验要求学生掌握缩丙酮化反应的机理(反Baldwin规则)和MestReNova软件的基本操作,可以加深学生对理论知识的理解并激发学生的学习兴趣。实验以“一锅”概念、反Baldwin规则为亮点,适用于本科生综合有机化学实验。
Ribose skeleton,widely existed in antiviral and mRNA drugs,plays an important role in drug discovery.However,the chemical transformation of ribose is rarely involved in the textbook of organic experiment for undergraduates.In this paper,the reaction of acetone ketalization and glycosylation of ribose with acetone and benzyl alcohol under acid catalysis is used to achieve the"one-pot"protection of the three hydroxyl groups of ribose.The reaction features cheap starting materials,mild conditions,and good reproducibility.And the work-up procedure involves a variety of experimental processes,which is perfectly suitable for training undergraduates'experimental skills.The experiment can deepen students'understanding of theoretical knowledge and stimulate their study interest through mechanism study of acetonization reaction(anti-Baldwin’s rules)and MestReNova software operation.The experiment highlights the concept of"one-pot"and anti-Baldwin’s rules,and is suitable for undergraduate comprehensive organic chemistry experiments.
作者
刘剑
赵周朋
王晓磊
Liu Jian;Zhao Zhoupeng;Wang Xiaolei(School of Pharmacy,Lanzhou University,Gansu,730000;College of Chemistry and Chemical Engineering,Lanzhou University,Gansu,730000)
出处
《当代化工研究》
2021年第23期122-124,共3页
Modern Chemical Research
基金
中央高校基本科研业务费专项资金(lzujbky-2021-69)。
关键词
本科生实验教学
核糖保护
有机化学
undergraduate laboratory teaching
ribose protection
organic chemistry
