Enzymatic resolution of (+-)-5-phenyl-4, 5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides (Articolo in rivista)

Type
Label
  • Enzymatic resolution of (+-)-5-phenyl-4, 5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides (Articolo in rivista) (literal)
Anno
  • 2009-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2009.07.025 (literal)
Alternative label
  • Cremonesi, G.; Croce, PD.; Forni, A.; Gallanti, M.; Gandolfi, R.; La Rosa, C. (2009)
    Enzymatic resolution of (+-)-5-phenyl-4, 5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides
    in Tetrahedron: asymmetry (Print); PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Cremonesi, G.; Croce, PD.; Forni, A.; Gallanti, M.; Gandolfi, R.; La Rosa, C. (literal)
Pagina inizio
  • 1940 (literal)
Pagina fine
  • 1947 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#altreInformazioni
  • IF 2009: 2.625; SJR 2009: Inorganic Chemistry, Q1 (literal)
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  • http://scienceserver.cilea.it.pros.lib.unimi.it/pdflinks/13062213225428898.pdf (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 20 (literal)
Rivista
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  • 8 (literal)
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  • 16 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopus (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • DISMAB--Sezione di Chimica Organica, Università degli Studi di Milano, 'A. Marchesini', V. Venezian 21, I-20133 Milano, Italy; Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, V. Venezian 21, I-20133 Milano, Italy; C.N.R.-I.S.T.M., Università degli Studi di Milano, V. Golgi,19, I-20133 Milano, Italy (literal)
Titolo
  • Enzymatic resolution of (+-)-5-phenyl-4, 5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides (literal)
Abstract
  • Enantiomerically pure (5R)-(-)-5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester was obtained via enzymatic resolution of the corresponding racemic mixture using a lipase from hog pancreas (PPL). The following reduction of the ester group to the corresponding alcohol and the oxidation of the latter led to (5R)-(-)-5-phenyl-4,5-dihydroisoxazole-3-carbaldehyde, and the reaction between this and Schollkopf's reagent, (2 R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine, gave mixtures of adducts with a good syn/anti ratio. The steric configurations of the major diastereoisomer were assigned on the basis of spectroscopic data and X-ray analysis. The subsequent controlled hydrolysis of the pyrazine ring led to beta-(5-phenyl-4,5-dihydroisoxazol-3-yl)-serine methyl esters and the corresponding dipeptides with (R)-valine. Finally, reductive cleavage of the 4,5-dihydroisoxazole ring under hydrolytic conditions made it possible to obtain the corresponding polyfunctionalised dipeptides. (literal)
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