文献类型：期刊文献

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

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

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Shanghai Key Lab New Drug Design, Sch Pharm,Minist Educ, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Hebrew Univ Jerusalem, Inst Chem, Safra Campus, IL-91904 Givat Ram, Israel

年份：2021

卷号：39

期号：12

起止页码：3309

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000705260000001)，CCR-EXPANDED(收录号:WOS:000705260000001)】；

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

语种：英文

外文关键词：Glycosides; Glycosylation; Protecting groups; Gold; Glycosyl ynenoates

摘要：Main observation and conclusion 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 excellent alpha-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.