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Synthesis 1987; 1987(12): 1110-1113
DOI: 10.1055/s-1987-28187
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The Regiospecific Alkylation of Histidine Side Chains

J. H. Jones* , D. L. Rathbone, P. B. Wyatt
  • *The Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, UK.
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Publication Date:
20 August 2002 (online)

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Further work on the regiospecific alkylation of histidine and imidazole derivatives is reported, including convenient preparations of N(α)-benzyloxycarbonyl-N(π)-benzyl-L-histidine and N(α)-benzyloxycarbonyl-N(π)-benzyloxymethyl-L-histidine, and a sequence of reactions enabling controlled exclusive alkylation of the least hindered im-nitrogen (tritylation, phenacylation, detritylation, alkylation, and finally dephenacylation with zinc/acetic acid) in 4(5)-alkylimidazoles.