@article { WOS:000705260000001, title = {Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides}, journal = {CHINESE JOURNAL OF CHEMISTRY}, volume = {39}, year = {2021}, note = {[[{"fid":"256182","view_mode":"default","type":"media","attributes":{"style":"width: 400px; height: 190px;","alt":"pho","class":"img-responsive media-element file-default "}}]] }, month = {DEC}, pages = {3309-3314}, abstract = {

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.\ 


}, issn = {1001-604X}, doi = {10.1002/cjoc.202100477}, author = {Li, Xiaoqian and Ma, Zhi and Liu, Rongkun and Mattan Hurevich and Yang, You} }