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

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

机构地区：[1]Shanghai Key Laboratory of New Drug Design,Engineering Research Center of Pharmaceutical Process Chemistry,Ministry of Education,School of Pharmacy,East China University of Science and Technology,130 Meilong Road,Shanghai 200237,China [2]Institute of Chemistry,Safra Campus,Givat Ram,Hebrew University of Jerusalem,91904,Israel

出　　处：《Chinese Journal of Chemistry》2021年第12期3309-3314,共6页中国化学（英文版）

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.

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.

关 键 词：GLYCOSIDES GLYCOSYLATION Protecting groups GOLD Glycosyl ynenoates 

分 类 号：O62[理学—有机化学]