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Protection of amines with the 4-azidomethylenoxybenzyloxycarbonyl group

✍ Scribed by Bernard Loubinoux; Philippe Gerardin

Book ID
104225404
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
191 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new urethane type protective group for amines, the 4-azidomethylenoxybenzyloxycarbonyl (AZ) group is described. This group is cleaved under very mild reductive conditions.It can be cleaved in the presence of the Z and methyl ester groups. Independent removal of AZ and BOC groups, each in the presence of the other, is possible.

The use of azidomethylenes

to block phenolic hydroxyls (1) has enabled us to develop a new protection method for carboxylic acids, useful for peptide synthesis (ABz group) (2). This method, characterized by mild deprotection conditions, makes it possible to obtain interesting selectivities. Following this observation, we used the same azidomethylene derivative for the protection of amines (AZ group).

πŸ“œ SIMILAR VOLUMES

Photolabile p-methoxyphenacyloxycarbonyl
Photolabile p-methoxyphenacyloxycarbonyl group for the protection of amines
✍ George Church; Jean-Marie Ferland; Jean Gauthier πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 214 KB

P-Methoxyphenacyloxycarbonyl (Phenoc) is a new photolabile protective group for ami nes. Various phenacyl urethanes, i.e. Phenoc protected amines, have been prepared. An appli cation of the group in peptide synthesis is reported. Various protective groups for amines are known'.