Journal article

THE FACILE ONE-POT SYNTHESIS OF N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-(O',O'-DIALKYLPHOSPHORO)- L-TYROSINES USING DIALKYL N,N-DIETHYLPHOSPHORAMIDITES

JW PERICH, EC REYNOLDS

SYNLETT | GEORG THIEME VERLAG KG | Published : 1991

Abstract

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.

University of Melbourne Researchers