A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4–SiO2

The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4–SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl β-d-furanosides with a 2-acetoxyisopropyl group.

Graphical abstractAn efficient procedure for the direct conversion of acetonides into acetates in the presence of HClO4–SiO2 under mild conditions was developed. The primary hydroxyl acetonides are directly transprotected to diacetates, and anomeric acetonides of furanosides are stereoselectively transformed into corresponding acetyl β-d-furanosides with a 2-acetoxyisopropyl group.Figure optionsDownload full-size imageDownload as PowerPoint slide