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Synthesis of orthogonally protected l-threo-β-ethoxyasparagine

Abstract:

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. © 2009 Springer-Verlag.