A Highly Efficient Azide-Based Protecting Group for Amines and Alcohols

The azide-based carbamate or carbonate protecting group (Azoc) shown above can be removed in less than 2 min under neutral conditions using trimethyl or tributyl phosphine as well as polymer-bound triphenyl phosphine. It was shown to be orthogonal to Fmoc and Mtt for peptide synthesis and to afford β-glycoside with a 2-aminoglucosyl donor by virtue of the neighboring group participation.