1421359-92-3Relevant academic research and scientific papers
Synthesis of enantiomerically pure isoxazolidine monomers for the preparation of β3-oligopeptides by iterative α-keto acid?￡?hydroxylamine (KAHA) ligations
Chiang, Ying-Ling,Russak, Justin A.,Carrillo, Nancy,Bode, Jeffrey W.
, p. 2481 - 2501 (2013/03/13)
A versatile method for the synthesis of enantiomerically pure isoxazolidine monomers for the synthesis of β3-oligopeptides via α-keto acidi?￡?hydroxylamine (KAHA) ligation is presented. This one-pot synthetic method utilizes in situ generated nitrones bearing gulose-derived chiral auxiliaries for the asymmetric 1,3-dipolar cycloaddition with methyl 2-methoxyacrylate. The resulting enantiomerically pure isoxazolidine monomers bearing diverse side chains (proteinogenic and non-proteinogenic) can be synthesized in either configuration (like- and unlike-configured). The scalable and enantioselective synthesis of the isoxazolidine monomers enables the use of the synthesis of β3-oligopeptides via iterative α-keto acidi?￡?hydroxylamine (KAHA) ligation. Copyright
