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Abstract:

Lipase-catalyzed alcoholysis of 2-thioacetoxyethyl acetate is described. Results depended on the biocatalyst, the nucleophile and the substrate/nucleophile ratio. When the reaction of the diester was carried out with one equivalent of 1-octanol under Candida antarctica lipase catalysis, it was found that 2-mercaptoethyl acetate is mainly obtained through S-acetyl removal.

Registro:

Documento: Artículo
Título:Lipase-catalyzed alcoholysis of 2-thioacetoxyethyl acetate
Autor:Iglesias, L.E.; Baldessari, A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1998
Volumen:86
Número:3-6
Página de inicio:203
Página de fin:207
Título revista:Anales des la Asociacion Quimica Argentina
ISSN:03650375
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p203_Iglesias

Referencias:

  • Wong, C.H., Whitesides, G.M., (1994) Tetrahedron Organic Chemistry Series, 12, p. 41. , Enzymes in synthetic organic chemistry (J.E. Baldwin Ed.), Pergamon
  • Koskinen, A.M.P., Klibanov, A.M., (1996) Enzymatic Reactions in Organic Media, , Chapman & Hall, Glasgow
  • Palmer, D.C., Terradas, F., (1994) Tetrahedron Lett., 35, p. 1673
  • Baldessari, A., Bruttomesso, A.C., Gros, E.G., (1996) Helv.Chim.Acta, 79, p. 999
  • Baldessari, A., Maier, M.S., Gros, E.G., (1995) Tetrahedron Lett., 36, p. 4349
  • Natoli, M., Nicolosi, G., Piattelli, M., (1992) J.Org.Chem., 57, p. 5776
  • Baldessari, A., Iglesias, L.E., Gros, E.G., (1992) J.Chem.Research, p. 204
  • Baldessari, A., Iglesias, L.E., Gros, E.G., (1994) Biotechnol.Lett., 16, p. 479
  • Iglesias, L.E., Baldessari, A., Gros, E.G., (1996) Bioorg.Med.Chem.Lett., 6, p. 853
  • Iglesias, L.E., Baldessari, A., Gros, E.G., (1998) An.Asoc.Quim.Argent., 86, p. 63
  • Iglesias, L.E., Baldessari, A., Gros, E.G., (1998) Biotechnol.Lett., 20, p. 275
  • Baldessari, A., Iglesias, L.E., Gros, E.G., (1993) J.Chem.Research, p. 382
  • Harding, J.S., Owen, L.N., (1954) J.Chem.Soc., p. 1528
  • Martin, R.B., Hedrick, R.I., (1962) J.Am.Chem.Soc., 84, p. 106
  • Ogino, K., Fujihara, H., (1992) Organic Sulfur Chemistry: Biochemical Aspects, p. 72. , p. 72, CRC Press, Boca Raton, Florida
  • Reference 2, p. 240; Moggridge, R.C.G., (1946) J.Chem.Soc., p. 1105

Citas:

---------- APA ----------
Iglesias, L.E. & Baldessari, A. (1998) . Lipase-catalyzed alcoholysis of 2-thioacetoxyethyl acetate. Anales des la Asociacion Quimica Argentina, 86(3-6), 203-207.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p203_Iglesias [ ]
---------- CHICAGO ----------
Iglesias, L.E., Baldessari, A. "Lipase-catalyzed alcoholysis of 2-thioacetoxyethyl acetate" . Anales des la Asociacion Quimica Argentina 86, no. 3-6 (1998) : 203-207.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p203_Iglesias [ ]
---------- MLA ----------
Iglesias, L.E., Baldessari, A. "Lipase-catalyzed alcoholysis of 2-thioacetoxyethyl acetate" . Anales des la Asociacion Quimica Argentina, vol. 86, no. 3-6, 1998, pp. 203-207.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p203_Iglesias [ ]
---------- VANCOUVER ----------
Iglesias, L.E., Baldessari, A. Lipase-catalyzed alcoholysis of 2-thioacetoxyethyl acetate. 1998;86(3-6):203-207.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p203_Iglesias [ ]