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四乙酰基-D-吡喃岩藻糖的合成

发表时间:2016-10-15  浏览量:1367  下载量:442
全部作者: 方静,朱阳斌,陈薇,刘艳,孙久常,曾静,万谦
作者单位: 华中科技大学药学院
摘 要: D-吡喃岩藻糖是很多具有重要生物活性的天然产物的结构组成单元,寻找D-吡喃岩藻糖的简便、高效和大规模合成方法对于完成此类天然产物的全合成具有重要意义。根据已报道的方法,研究以D-半乳糖为原料,通过优化反应条件,依次经丙酮叉保护、对甲基苯磺酸酯化、碘代、脱碘、去丙酮叉保护基和乙酰化五步反应,最终以53%的总产率得到四乙酰基-D-吡喃岩藻糖,实现了四乙酰基-D-吡喃岩藻糖10 g级的大规模制备。与已报道方法相比,本方法成本低、操作简便、效率更高,为大规模制备D-吡喃岩藻糖提供了新的选择。
关 键 词: 有机化学;稀有糖;D-吡喃岩藻糖;D-半乳糖
Title: Synthesis of tetraacetyl-D-fucopyranose
Author: FANG Jing, ZHU Yangbin, CHEN Wei, LIU Yan, SUN Jiuchang, ZENG Jing, WAN Qian
Organization: School of Pharmacy, Huazhong University of Science and Technology
Abstract: D-fucopyranose is an important component of many bioactive natural products. Development of efficient and practical synthetic strategy for large scale synthesis of D-fucopyranose is of great importance for the total synthesis of these natural products. Based on the optimization of reported synthetic methods, herein, we reported a 10 g-scale synthesis of tetraacetyl-D-fucopyranose in 5 steps with 53% total yield from D-galactose through sequential acetonation, sulfonation, iodination, deiodination and acetylation. Compared to the reported methods, this method has the advantages of low cost, easy manufacture and high efficiency, which offers an alternative for the large scale synthesis of D-fucopyranose.
Key words: organic chemistry; rare sugar; D-fucopyranose; D-galactose
发表期数: 2016年10月第19期
引用格式: 方静,朱阳斌,陈薇,等. 四乙酰基-D-吡喃岩藻糖的合成[J]. 中国科技论文在线精品论文,2016,9(19):2030-2034.
 
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