Azidomethyl Carbamate and Carbonate: Cleavage with Polymeric Phosphine

Significance

Winssinger and Pothukanuri proposed the N- or O-COOCH₂N₃ unit as a carbamate- or carbonate-type protecting group (Azoc). Thus, the azidomethyl carbamate (N-Azoc) was readily introduced into a primary amine (e.g. 1) by a reaction with chloromethyl chloroformate followed by azidation with sodium azide. The deprotection was performed with trimethylphosphine, tributylphosphine, or polystyrene-supported triaryl­phosphine in aqueous-organic media at ambient temperature. The Azoc group was introduced into and detached from aminoglucose 3 and glycoside 5 without any side reactions.