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

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

机构地区:[1]College of Science,Nanjing Forestry University,Nanjing 210037,China [2]State Key Laboratory of Natural and Biomimetic Drugs,School of Pharmaceutical Sciences,Peking University,Beijing 100191,China [3]Department of Biomolecular Engineering,Graduate School of Engineering,Tohoku University,Sendai 980-8579,Japan

出  处:《Chinese Chemical Letters》2023年第4期313-317,共5页中国化学快报(英文版)

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。

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.

关 键 词:O-GLYCOSYLATION Hydrogen bond α-Selectivity GLYCOLIPID Natural product 

分 类 号:O629.13[理学—有机化学]

 

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