【作者】 肖雄； 赵翔； 舒朋华； 赵岳琦； 刘艳； 孙久常； 曾静； 万谦；

【Author】 Xiong Xiao;Xiang Zhao;Penghua Shu;Yueqi Zhao;Yan Liu;Jiuchang Sun;Jing Zeng;Qian Wan;Tongji School of Pharmacy, Huazhong University of Science and Technology;

【机构】 华中科技大学同济医学院药学院；

【摘要】 糖苷键的构造是糖化学研究的关键和核心问题,发展新颖而有效的糖苷化方法并应用于寡糖尤其是糖类药物及疫苗的合成是糖科学家面临的巨大挑战之一。通过利用Interrupted Pummerer反应,我们以远程活化的方式激活了离去基,成功的实现糖苷键的高效立体选择性构建。该策略广泛适用于各种活性的供体和受体,也成功的应用于多个具有生物活性的天然寡糖的全合成。更多还原

【Abstract】 Glycosidic bond formation plays the central role in carbohydrate chemistry.Despite great efforts have been made,it is still a big challenge to development of new and efficient glycosylation strategies for the polysaccharide synthesis.Inspired by the Pummerer reaction reported early in 1909,we have developed a novel glycosylation strategy by designing a new type of anomeric leaving groups which could be obtained by selectively oxidizing corresponding thiol ethers.Through remote activation of the sulfoxide functional groups,the stereoselective glycosidic bond formation among various of glycosyl donors and acceptors was successfully achieved.In addition,this strategy was also applied to the total synthesis of naturally occurring polysaccharides with important bioactivities.更多还原