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Synthesis 1989; 1989(9): 701-703
DOI: 10.1055/s-1989-27366
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An Improved One-pot Synthesis of N α-(tert-Butoxycarbonyl)- O-(O′,O″-dialkylphosphoro)-L-tyrosines Using Dialkyl N,N-Diethylphosphoramidites

John W. Perich* , R. B. Johns
  • *Department of Organic Chemistry, University of Melbourne, Parkville, 3052, Victoria, Australia
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Publication Date:
17 September 2002 (online)

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N α-(tert-Butoxycarbonyl)-O-(O′,O″-dialkylphosphoro)-L-tyrosines 6a-c were prepared in high yields by an efficient one-pot procedure, which involved initial tert-butyldimethylsilyl protection of the carboxy terminus of N-Boc tyrosine 1 followed by successive in situ phosphitylation of the tyrosyl hydroxyl group, oxidation of the resultant phosphite triester and deprotection.

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