Hydrogen bond-assisted 1,2-cis O-glycosylation under mild hydrogenolytic conditions

作     者：Gefei Li Yanlong Luo Juan Mo Masato Noguchi Jie Jing Zhenyang Luo Shin-ichiro Shoda Xin-Shan Ye Gefei Li;Yanlong Luo;Juan Mo;Masato Noguchi;Jie Jing;Zhenyang Luo;Shin-ichiro Shoda;Xin-Shan Ye

作者机构：College of ScienceNanjing Forestry UniversityNanjing 210037China State Key Laboratory of Natural and Biomimetic DrugsSchool of Pharmaceutical SciencesPeking UniversityBeijing 100191China Department of Biomolecular EngineeringGraduate School of EngineeringTohoku UniversitySendai 980-8579Japan 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2023年第34卷第4期

页      面：313-317页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：financially supported by the State Key Laboratory of Natural and Biomimetic Drugs (No. K202216) the National Natural Science Foundation of China (Nos. 21907004 and 81821004) the National Key R&D Program of China (No.2018YFA0507602) the Beijing Outstanding Young Scientist Program(No. BJJWZYJH01201910001001) a Grant-in-Aid for Scientific Research from the Ministry of Education,Culture,Sports,Science and Technology,Japan 

主　　题：O-Glycosylation Hydrogen bond α-Selectivity Glycolipid Natural product 

摘      要：A hydrogen bond-assisted α-selective glycosylation reaction by using 4,6-dibenzyloxy-1,3,5-triazin-2-yl(DBT) β-glycosyl donors was developed for the efficient construction of 1,2-cis-α-glycosidic bond in natural products. This method was applied successfully to the direct synthesis of complex oligosaccharidederived glycolipids with simple protecting chemistry. Mechanistic studies using the NMR spectroscopy and DFT calculation provide a proof of concept for hydrogen bond-assisted glycosylation reaction towardsα-specific construction of O-glycosidic linkage.