Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides

作     者：Xiaoqian Li Zhi Ma Rongkun Liu Mattan Hurevich You Yang Xiaoqian Li;Zhi Ma;Rongkun Liu;Mattan Hurevich;You Yang

作者机构：Shanghai Key Laboratory of New Drug DesignEngineering Research Center of Pharmaceutical Process ChemistryMinistry of EducationSchool of PharmacyEast China University of Science and Technology130 Meilong RoadShanghai 200237China Institute of ChemistrySafra CampusGivat RamHebrew University of Jerusalem91904Israel 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：2021年第39卷第12期

页      面：3309-3314页

核心收录：

学科分类：07[理学] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：Financial support from the National Natural Science Foundation of China(21871081,22071054) the Fundamental Research Funds for the Central Universities(50321031916002,22221818014)is gratefully acknowledged. 

主　　题：Glycosides Glycosylation Protecting groups Gold Glycosyl ynenoates 

摘      要：A green and efficient photolabile protecting group(PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported.By employing ortho-nitrobenzyl carbonate(oNBC)as PPG,N,N-dimethylformamide(DMF)-modulated SPhosAuNTf_(2)-promoted glycosidation with per-oNBC-protected 2-deoxy-glycosyl ynenoates affords the 2-deoxy-glycosides with moderate to excellentα-selectivities presumably depending on the reactivities of the acceptor alcohols.Based on the PPG-mediated glycosidation approach,oligosaccharides with three to six oNBC groups are effectively achieved.The multiple oNBC groups in the 2-deoxy-glycosides are completely cleaved by irradiation at 365 nm,resulting in the desired 2-deoxy-glycosides in an efficient manner without affecting the common alkyne,alkene,azide functional groups and the traditional protecting groups on the aglycones.