Synlett 2014; 25(15): 2166-2170
DOI: 10.1055/s-0034-1378532
letter
© Georg Thieme Verlag Stuttgart · New York

Direct Synthesis of Polybenzylated Glutamic Acid Monoesters: Disambiguation of N,N-Dibenzylglutamic Acid α- and γ-Benzyl Esters

Gastón Silveira-Dorta
Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain   Fax: +34(922)318571   Email: jmpadron@ull.es
,
Víctor S. Martín
Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain   Fax: +34(922)318571   Email: jmpadron@ull.es
,
José M. Padrón*
Instituto Universitario de Bio-Orgánica ‘Antonio González’ (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain   Fax: +34(922)318571   Email: jmpadron@ull.es
› Author Affiliations
Further Information

Publication History

Received: 15 May 2014

Accepted after revision: 25 June 2014

Publication Date:
13 August 2014 (online)


Abstract

In this study, we explored the regioselective benzylation of l-glutamic acid under substoichiometric amounts of the alkylating agent. Our results demonstrate unambiguously that N,N-dibenzylglutamic acid γ-benzyl ester was not obtained by direct benzylation of l-glutamic acid as reported by other authors. Instead, under such reaction conditions N,N-dibenzylglutamic acid α-benzyl ester was obtained.

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