杨梅素-3-O-β-D-乳糖的合成方法优化  

Optimization of Synthesis Method of Myricetin-3-O-β-D-lactose

作　　者：李冬洋 姜磊磊 代兴隆 万升标[1,2] LI Dongyang;JIANG Leilei;DAI Xinglong;WAN Shengbiao(Key Laboratory of Marine Drugs,Ministry of Education,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China;Pilot National Laboratory of Qingdao Marine Science and Technology,Qingdao 266237,China)

机构地区：[1]中国海洋大学医药学院海洋药物教育部重点实验室,山东青岛266003 [2]青岛海洋科学与技术试点国家实验室,山东青岛266237

出　　处：《合成化学》2023年第12期962-967,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(82273777)。

摘　　要：杨梅素是一种主要用于抗炎的多酚类黄酮化合物,为改善其水溶性和稳定性,合成了杨梅素-3-O-β-D-乳糖,并开发了一条高效的合成路线。首先以杨梅苷为起始原料,对杨梅苷的5位、7位、3′位、4′位和5′位酚羟基进行保护,形成五苄基保护的杨梅苷。然后脱除3位鼠李糖,再与乙酰基保护的乳糖溴苷反应,最后通过依次脱去乙酰基和苄基得到目标化合物。经过路径优化,最终以更高效的方法合成了杨梅素-3-O-β-D-乳糖,减少了副产物的生成,提高了原合成路线总收率,此方法的总产率为44.5%。该路径得到了2个新型的杨梅素衍生物中间体。目标化合物的结构均经过1 H NMR,13 C NMR和HR-MS(ESI)确证。Myricetin is a polyphenol flavonoid mainly used for anti-inflammation.In order to improve its water solubility and stability,myricetin-3-O-β-D-lactose was synthesized and its efficient synthetic route was developed.myricetrin was used as the starting material,and all the phenolic hydroxyl groups at 5,7,3′,4′,5′positions of myricetrin were protected with benzyl.Then rhamnose at 3 position was removed,and it reacted with acetobromolactose.Finally,the target compound was obtained by sequentially removing acetyl group and benzyl group.myricetin-3-O-β-D-lactose was synthesized by a more efficient method,which reduced the generation of by-products and improved the total yield of the original synthetic route.The total yield of this method was 44.5%,and two new intermediates of myricetin derivatives were obtained.The structures of the synthesized compounds were confirmed by^(1)H NMR,^(13)C NMR and HR-MS(ESI).

关 键 词：杨梅素 杨梅苷 碳酸铯 乙酰基乳糖溴苷 杨梅素-3-O-β-D-乳糖 合成方法 

分 类 号：O629.9[理学—有机化学]