3,3ʹ,5,5ʹ-Tetramethoxybenzoin: a forgotten photolabile protecting group

Abstract

Although reported several decades ago, 3,3',5,5'-tetramethoxybenzoin esters have not been used as a common photolabile protecting group, contrary to their unsymmetrical 3',5'-dimethoxybenzoin analogues. While the properties of the latter are superior, their tedious synthesis and chemical instability represent a drawback. In this article, we describe a reliable synthetic access to the symmetrical tetramethoxybenzoin derivatives, and show that their photochemical behaviour remain interesting, in particular chromatically orthogonality with respect to nitroveratryl esters.