674790-23-9Relevant academic research and scientific papers
Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives
Middleton, Richard J.,Mellor, Sarah L.,Chhabra, Siri Ram,Bycroft, Barrie W.,Chan, Weng C.
, p. 1237 - 1242 (2007/10/03)
A concise synthesis of novel homochiral aromatic amino acid surrogates comprising a tetrahydroindazole or a benzisoxazole system was developed via the acylation of a cyclic 1,3-diketone by the side-chain carboxyl functionality of either Boc-Asp-OtBu or Boc-Glu-OtBu followed by regioselective condensation with hydrazine, N-benzylhydrazine and hydroxylamine. The tetrahydroindazole nucleus was also constructed by the condensation of Boc-Asp-OtBu with the enamine, 1-pyrrolidino-1-cyclohexene followed by acid-hydrolytic treatment and reaction with hydrazines. Further functional group transformations gave N α-Fmoc-protected derivatives as useful building blocks for solid-phase peptide assembly.
