Photolabile Protecting <scp>Group‐Mediated</scp> Synthesis of <scp>2‐Deoxy‐Glycosides</scp>
Xiaoqian Li, Zhi Ma, Rongkun Liu, Mattan Hurevich, You Yang
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 ( o NBC) as PPG, N , N ‐dimethylformamide (DMF)‐modulated SPhosAuNTf 2 ‐promoted glycosidation with per‐ o NBC‐protected 2‐deoxy‐glycosyl ynenoates affords the 2‐deoxy‐glycosides with moderate to excellent α‐selectivities presumably depending on the reactivities of the acceptor alcohols. Based on the PPG‐mediated glycosidation approach, oligosaccharides with three to six o NBC groups are effectively achieved. The multiple o NBC 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.