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Publication 46  

  1. A Highly Efficient Azide-Based Protecting Group for Amines and Alcohols
    S. Pothukanuri, N. Winssinger
    Org. Lett. 2007, 9, 2223-2225

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.

DOI: 10.1021/ol0707160 

open archive unige:24445