synthesis of rac-tert-butyl 3-(benzyloxycarbonylamino)-2-(4-bromophenyl)-tetrahydrofuran-3-carboxylaterac-tert-butyl 3 -(benzyloxycarbonylamino)的合成2 -(4-bromophenyl)-tetrahydrofuran-3-carboxylate.pdfVIP

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synthesis of rac-tert-butyl 3-(benzyloxycarbonylamino)-2-(4-bromophenyl)-tetrahydrofuran-3-carboxylaterac-tert-butyl 3 -(benzyloxycarbonylamino)的合成2 -(4-bromophenyl)-tetrahydrofuran-3-carboxylate.pdf

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synthesis of rac-tert-butyl 3-(benzyloxycarbonylamino)-2-(4-bromophenyl)-tetrahydrofuran-3-carboxylaterac-tert-butyl 3 -(benzyloxycarbonylamino)的合成2 -(4-bromophenyl)-tetrahydrofuran-3-carboxylate

Molbank 2009, M596 OPEN ACCESS molbank ISSN 1422-8599 /journal/molbank Short Note Synthesis of rac-tert-butyl 3-(benzyloxycarbonylamino)-2-(4- bromophenyl)-tetrahydrofuran-3-carboxylate Andreas Grauer and Burkhard König* Institute of Organic Chemistry, University of Regensburg, D-93040 Regensburg, Germany * Author to whom correspondence should be addressed. E-mail: Burkhard.koenig@chemie.uni-regensburg.de Received: 21 February 2009 / Accepted: 12 March 2009 / Published: 23 March 2009 α Abstract: A new C -tetrasubstituted α-amino acid rac-tert-butyl 3- (benzyloxycarbonylamino)-2-(4-bromophenyl)-tetrahydrofuran-3-carboxylate was synthesized and characterized by NMR, MS, elemental analysis and X-ray. Keywords: amino acid synthesis, Cα-tetrasubstituted α-amino acids, unnatural amino acids Introduction Cα-Tetrasubstituted α-amino acids are important molecules for the synthesis of peptidemimetics with stabilized secondary structure, because of their ability to rigidify the peptide backbone [1–7]. Recently we developed a tetrahydrofuran based Cα-tetrasubstituted α-amino acid which is Boc- protected at the N-terminus and tbutyl protected at the C-terminus [8]. Unfortunately, these two protecting groups are not entirely orthogonal: Cleavage of the Boc-group with HCl saturated diethyl ether is possible in the presence of the tbutyl-ester, but the ester group cannot be saponified without cleaving the Boc-group. Therefore we decided to synthesiz