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Synlett 1991; 1991(8): 577-578
DOI: 10.1055/s-1991-20804
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The Facile One-Pot Synthesis of N α-(9-Fluorenylmethoxycarbonyl)-O-(O′, O″-dialkylphosphoro)-L-tyrosines Using Dialkyl N,N-Diethylphosphoramidites

John W. Perich* , Eric C. Reynolds
  • *Biochemistry and Molecular Biology Unit, School of Dental Science, The University of Melbourne, 711 Elizabeth St., Melbourne, 3000, Victoria, Australia
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Publication Date:
07 March 2002 (online)

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N α-(9-Fluorenylmethoxycarbonyl)-O-(O′, O″-dialkylphosphoro)-L-tyrosines (R = methyl, benzyl, tert-butyl) were prepared in high yield by a facile one-pot procedure which involved initial tert-butyldimethylsilyl protection of the carboxy terminus of N-Fmoc tyrosine followed by in situ phosphitylation of the tyrosyl hydroxyl group using dimethyl, dibenzyl or di-tert-butyl N,N-diethylphosphoramidite/1H-tetrazole, oxidation of the resultant dialkyl phosphite triester with tert-butyl hydroperoxide and finally cleavage of of the carboxy silyl group by mild acidolysis.