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Synthesis of Phenylalanine Analogs
Author(s) -
Chang MengYang,
Lin ChunYu,
Sun PeiPei
Publication year - 2005
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200500150
Subject(s) - chemistry , phenylalanine , sodium azide , yield (engineering) , ammonium acetate , organic chemistry , cerium , azide , sodium acetate , ammonium nitrate , amino acid , biochemistry , materials science , high performance liquid chromatography , metallurgy
A straightforward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamic ester, followed by reaction with sodium acetate afforded the α‐azidocinnamate in moderate yield. Hydrogenation of α‐azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p ‐boronophenylalanine analog was also explored.