Tetrahedron p. 3369 - 3382 (1997)
Update date:2022-09-26
Topics:
Lloyd-Williams, Paul
Sanchez, Agusti
Carulla, Natalia
Ochoa, Teresa
Giralt, Ernest
N-Acetylated threonine derivatives, having tert-butyl or benzyl-based side-chain protection, form isolable 5(4H)-oxazalones on treatment with N-ethyl-N'-3-dimethylaminopropyl carbodiimide. N-chloroacetylated threonine derivatives, on the other hand, do not form oxazolones so readily. The N-acetylated oxazolones an easily epimerized and lead to diastereoisomeric mixtures of threonine derivatives on hydrolysis with dilute aqueous acid. The components of these mixtures can be separated chromatogaphically, but a useful alternative for the O-benzylated mixture is selective enzymatic hydrolysis using hog kidney acylase. These chemical transformations provide the basis for practical syntheses of protected derivatives of the non-proteinogenic allo-threonines, suitable for use in peptide synthesis.
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Doi:10.1002/anie.199711941
(1997)Doi:10.1021/acs.orglett.1c00898
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(2000)Doi:10.1002/aoc.6065
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