4-Nitrobenzyl Group for Protection of Hydroxyl Functions

Fukase, K.; Tanaka, H.; Torii, S.; Kusumoto, S. Tetrahedron Lett. 1990, 31, 389.

Versatile use of 4-nitrobenzyl group for protection of hydroxyl functions is described. It can be removed selectively in the presence of other benzyl-type protecting groups such as benzyl and 4-methoxybenzyl via reduction into 4-amino-benzyl group followed by electrochemical oxidation. Very clean oxidative cleavage of 4-aminobenzyl group could also be effected with 2,3-dichloro-5,6-dicyanobenzoquinone after N-acetylation.