Add time:09/06/2019 Source:sciencedirect.com
(R)-2-Azidoesters and their derived (R)-2-azido acids are readily prepared from common amino acids by an inversion methodology that employs (S)-2-nosyloxyesters as key intermediates. The (R)-2- azidoesters can be used as protected amino acid equivalents in peptide synthesis. Basic hydrolysis frees the carboxyl group. Triphenylphosphine/water is used to free the amine group. By these reactions a variety of L- D and D-L dipeptides,L-D-L tripeptides,and depsipeptides can be prepared easily in good yields, and without detectable epimerization.
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