Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution (Articolo in rivista)

Type
Label
  • Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution (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.2009.02.026 (literal)
Alternative label
  • C. Carnovale; D. Iannazzo; G. Nicolosi; A.Piperno; C. Sanfilippo (2009)
    Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • C. Carnovale; D. Iannazzo; G. Nicolosi; A.Piperno; C. Sanfilippo (literal)
Pagina inizio
  • 425 (literal)
Pagina fine
  • 429 (literal)
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  • 20 (literal)
Rivista
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  • 5 (literal)
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  • 4 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento Farmaco-Chimico, Università di Messina, Viale SS. Annunziata, 98168 Messina, Italy; Istituto di Chimica Biomolecolare, C.N.R, Via P. Gaifami, 18, 95126 Catania, Italy (literal)
Titolo
  • Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution (literal)
Abstract
  • An efficient biocatalytic procedure to obtain chiral N,O-nucleoside derivatives consisting of a lipase-catalysed resolution of the corresponding racemates in organic solvent has been developed. Enantioselective esterification of thymine and cytosine derivatives, (±)-9a and (±)-9b, has been investigated by comparing the efficiency of different lipases and acyl donors. Since esterification of (±)-9a and (±)-9b, occurred with low enantioselectivity (E <= 14) in the presence of the lipases considered, for preparative purposes we resorted, with success, to a double sequential kinetic resolution, using Lipozyme IM as the best catalyst. This approach enables us to obtain all the enantiomers with ee >= 95%. The absolute configuration of the new chiral N-acetyl cytosine derivative 9b was established by circular dichroism spectroscopy. (literal)
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