1239998-32-3Relevant academic research and scientific papers
Synthesis of orthogonally protected l-threo-β-ethoxyasparagine
Spengler, Jan,Pelay, Marta,Tulla-Puche, Judit,Albericio, Fernando
experimental part, p. 161 - 165 (2010/09/08)
Orthogonally protected l-threo-β-ethoxyasparagine (Fmoc-EtOAsn(Trt)- OH, 1) was synthesized from diethyl (2S,3S)-2-azido-3-hydroxysuccinate 2 in eight steps as a building block for solid-phase peptide synthesis. The starting material is easily available in multi-gram scale from d-diethyltartrate. The transformation steps reported here are robust and scalable. Thus, a significant amount of 1 (1.8 g) was obtained in 21% overall yield. The synthesis reported is also expected to be useful for the preparation of other O-substituted l-threo-β-hydroxyasparagine derivatives.
