通过金（I）催化的甘露吡喃糖基邻己炔基苯甲酸酯的糖基化反应构建β-甘露糖苷键及其在顶头孢菌素甘露脂A合成中的应用。
Construction of β-mannosidic bonds via gold(I)-catalyzed glycosylations with mannopyranosyl ortho-hexynylbenzoates and its application in synthesis of acremomannolipin A.
作者信息
Sun Peng, Wang Peng, Zhang Yongzhen, Zhang Xiuli, Wang Cong, Liu Shaojing, Lu Jinjie, Li Ming
机构信息
†Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
‡State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, P. R. China.
出版信息
J Org Chem. 2015 Apr 17;80(8):4164-75. doi: 10.1021/acs.joc.5b00140. Epub 2015 Apr 3.
A mild and convenient protocol for direct synthesis of β-mannosides has been developed. Glycosylation of 4,6-O-benzylidene-protected mannosyl ortho-hexynylbenzoates with various alcohol acceptors catalyzed by gold(I) complex proceeded smoothly at 0 °C to room temperature and afforded the corresponding β-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.
已开发出一种温和且简便的直接合成β-甘露糖苷的方法。在金（I）配合物催化下，4,6-O-亚苄基保护的甘露糖基邻己炔基苯甲酸酯与各种醇受体进行糖基化反应，在0℃至室温下顺利进行，以高产率和令人满意的立体选择性得到相应的β-甘露糖苷。该反应应用于顶头孢菌素A及其类似物的全合成。
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