微波辅助合成甘露糖基三氯乙酰亚胺酯及其传统方法优化
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微波辅助合成甘露糖基三氯乙酰亚胺酯及其传统方法优化

Microwave Assisted Synthesis of Mannosyl Trichloroacetimidate and Its Process Improvement on Traditional Synthetic Method

DOI:10.3969/j.issn.1673-1689.2014.07.009

中文关键词: 甘露糖基三氯乙酰亚胺酯 工艺优化 微波辅助

英文关键词: mannosyl trichloroacetimidate, process improvement, microwave assisted

基金项目:

作者

单位

王伟

江南大学 食品学院江苏 无锡 214122

成向荣

江南大学 食品学院江苏 无锡 214122

食品科学与技术国家重点实验室江南大学江苏 无锡 214122

施用晖

江南大学 食品学院江苏 无锡 214122

食品科学与技术国家重点实验室江南大学江苏 无锡 214122

乐国伟

江南大学 食品学院江苏 无锡 214122

食品科学与技术国家重点实验室江南大学江苏 无锡 214122

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中文摘要:

甘露聚糖及甘露糖蛋白在很多生理过程中扮演重要的角色,它们的合成研究也是目前糖化学热点之一,甘露糖基三氯乙酰亚胺酯是它们合成中十分有效的糖给体。研究了甘露糖基三氯乙酰亚胺酯新型微波辅助合成方法,并对传统合成方法进行优化改进。以D-甘露糖为原料,通过全苯甲酰基化、端位选择性水解,再与三氯乙腈反应合成了2,3,4,6-四-O-苯甲酰基-β-D-甘露糖三氯乙酰亚胺酯,对传统合成方法进行了优化,使得总产率达到85%以上。同时首次通过微波辅助的方法合成了该种产物,结果表明,微波辅助合成方法产物产率是传统方法的1.12倍,合成时间缩短了15倍。

英文摘要:

Mannose-oligosaccharides and mannose glycoprotein play an important role in many physiological processes, their synthesis is a vital branch of carbohydrate chemistry. Mannosyl trichloroacetimidate is a very efficient glycosyl donor in their synthesis. This paper investigated the new microwave assisted synthesis of mannosyl trichloroacetimidate, and optimized the traditional synthetic method. It was synthesized from D-mannose by benzoyl protection, hydrolysis and then reaction with trichloroacetonitril. Its existing methods were optimized and total yield was more than 85%. Meanwhile it was synthesized by the microwave assisted method firstly. The experiment result indicated the total yield in new method was more than 12% compared with that in traditional method, while the reaction time was shortened about 15 times.

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