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Synthesis 1990; 1990(6): 531-532
DOI: 10.1055/s-1990-26931
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Improved Procedures for the Synthesis of N,N-Diallyltyrosine Intermediates

Eduard Bardaji* , Josep Lluís Torres, Núria Xaus, Pere Clapés, Xavier Jorba, Beatriz G. de la Torre, Gregorio Valencia
  • *Unit for Peptide Chemistry and Biochemistry, Centre d'Investigació i Desenvolupament (C.S.I.C.) Jordi Girona 18-26, E-08034 Barcelona, Spain
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Publication Date:
17 September 2002 (online)

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N,N-Diallyltyrosine allyl ester bearing a base-labile phenol protecting group can be obtained from O-benzyloxycarbonyltyrosine by a one-step allylation with allyl bromide. This allyl ester is efficiently deprotected with morpholine in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) or by alkaline cleavage of the O-benzyloxycarbonyl group followed by enzymatic hydrolysis using α-chymotrypsin.