4-Nitrobenzyl group for protection of hydroxyl functions

✍ Scribed by Koichi Kukase; Hideo Tanaka; Sigeru Toriib; Shoichi Kusumoto

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 322 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)94562-3

✦ Synopsis

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-aminobenzyl 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.