Visible‐light‐mediated Oxidative Debenzylation of 3‐ O ‐Benzyl‐1,2:5,6‐di‐ O ‐isopropylidene‐α‐D‐glucofuranose

Abstract

Abstract This chapter presents the procedure for the visible‐light‐mediated oxidative debenzylation of 3‐O‐benzyl‐1,2:5,6‐ di‐O‐isopropylidene‐α‐d‐glucofuranose . Benzyl ethers are important protective groups in the synthesis of carbohydrates due to their excellent stability over a wide range of conditions. However, benzyl ether cleavage requires harsh reduction/oxidation processes, such as catalytic hydrogenolysis, Birch reduction, or oxidation with ozone or BCl, that are hazardous, and poorly functional group tolerant. The photooxidative debenzylation strategy overcomes current limitations of benzyl ethers as protecting groups that arise from the harsh conditions necessary for their cleavage. The methodology enables the use of benzyl ethers as orthogonal protective group that is installed and removed throughout the synthesis of complex molecules and clears the path to the development of new synthetic routes in total synthesis.