文献类型：期刊文献

中文题名：Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides

作者：Xiaoqian Li[1];Zhi Ma[1];Rongkun Liu[1];Mattan Hurevich[2];You Yang[1]

机构：[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

年份：2021

卷号：39

期号：12

起止页码：3309

中文期刊名：Chinese Journal of Chemistry

外文期刊名：中国化学（英文版）

收录：CSTPCD;;Scopus;CSCD:【CSCD2021_2022】；PubMed;

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.

语种：英文

中文关键词：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.