Ultrasound-Assisted Selective Deprotection of Terminal Acetonides Catalyzed by Silica-Supported Boron Trifluoride

Abstract

An efficient and convenient method for the selective cleavage of terminal acetonides is described. Treatment of terminal acetonides in the presence of a wide range of functional groups with silica-supported boron trifluoride as a catalyst furnished the corresponding diols in 82–95% yield under ultrasound irradiation conditions. The acid-labile p-methoxybenzyl group as a protecting group remained intact under the conditions employed to the present deprotection condition.

Keywords:

• Carbohydrate
• Acetonide
• Ultrasound
• Silica-supported
• Boron trifluoride

ACKNOWLEDGMENTS

This work was supported by the National Nature Science Foundation of China (No. 210022014 and 81072525).