文献类型：期刊文献

英文题名：Photolabile ortho-Nitro-Benzyl Carbonate as an Amino Protecting Group for Stereocontrolled Synthesis of 2-Amino-2-Deoxy-β-d-Glycosides

作者：Shang, Jintao[1];Wang, Yi[1];Chang, Dongsheng[1];Zheng, Jibin[1];Chen, Hongyu[1];Yao, Shuang[1];Yang, You[1,2]

机构：[1]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Met, Sch Pharm, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Minist Educ, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2025

卷号：28

期号：6

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001367462400001)】；

基金：Financial support from the National Natural Science Foundation of China (22071054, 21871081), the Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission), and the Taishan Industrial Experts Program (tscx202312168) is gratefully acknowledged.

语种：英文

外文关键词：carbohydrates; protecting groups; glycosylation; glycosides; gold

摘要：Traditional amino protecting groups are often removed under harsh conditions or incompatible with other protecting groups, rendering the synthesis of complex 2-amino-2-deoxy-beta-d-glycosides difficult. Here, we utilize the photolabile ortho-nitrobenzyl carbonate (oNBC) as an amino protecting group for stereocontrolled synthesis of 2-amino-2-deoxy-beta-d-glycosides. The gold(I)-catalyzed glycosylation with per-O-oNBC-protected 2-N-phthaloyl (Phth)-2-deoxy-, 2-N-trichloroacetyl (TCA)-2-deoxy-, and 2-N-oNBC-2-deoxy-glycosyl ynenoates proceeded smoothly to provide 2-amino-2-deoxy glycosides with exclusive beta-selectivities via the neighboring group participation (NGP) effect. Removal of the multiple O- and N-oNBC protecting groups of 2-amino-2-deoxy glycosides was achieved under irradiation at 365 nm with aminomethyl polystyrene as the carbonyl scavenger.