683228-01-5Relevant academic research and scientific papers
Ring-opening of oxazolines derived from l-serine: a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives
Lee, Sang-Hyeup,Bok, Juhan,Qi, Xin,Kim, Sook Kyung,Lee, Yoon-Sik,Yoon, Juyoung
, p. 7309 - 7312 (2007)
Facile methods are described for accessing four diastereomerically pure 3-mercaptoaspartic acid derivative from l-aspartic acid. In our synthesis, ring-opening reactions of oxazoline-4,5-dicarboxylate with thiolacetic acid as well as the stereochemical interconversion of both α- and β-configuration via oxazoline chemistry were utilized as key steps.
An efficient approach to D-threo-3-hydroxyaspartic acid for the synthesis of novel L-threo-oxazolines as selective blockers of glutamate reversed uptake
De Angelis, Meri,Campiani, Giuseppe
, p. 2355 - 2357 (2007/10/03)
An efficient, stereoselective synthetic strategy to D-threo-3- hydroxyaspartic acid was developed. Starting from L-(2S,3S)-N-benzoyl-3- hydroxyaspartic acid dimethyl ester by a Deoxo-fluor-catalyzed cyclization reaction, an inversion of configuration at the β-center (erythro isomer), was observed. A base-induced epimerization reaction led to the D-trans-isomer, which was hydrolyzed to give D-threo-3-hydroxyaspartic acid with excellent stereoselectivity and overall yield. Starting from D-threo-3-hydroxyaspartic acid, L-threo-oxazolines can be stereoselectively synthesized.
