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Abstract:

The known 1,4-anhydro-2,3,6-tri-O-benzyl-D-galactopyranose (1) has been regioselectively ring-opened using a variety of nucleophiles under acidic conditions to exclusively afford furanosides.

Registro:

Documento: Artículo
Título:Synthesis of galactofuranosides by regioselective ring opening of a 1,4-anhydrogalactopyranose derivative: A possible chemical model for an unprecedented enzymatic reaction
Autor:Kovensky, J.; Sinaÿ, P.
Filiación:CIHIDECAR (CONICET), Departamento de Química Orgánica, Pabellón II, 1428 Buenos Aires, Argentina
Département de Chimie, Associé au CNRS, Ecole Normale Supérieure, 24, rue Lhomond, 75231 Paris Cedex 05, France
Palabras clave:Anhydro sugars; Carbohydrates; Enzymes; Galactofuranosides; Glycosides; 1,4 anhydro 2,3,6 tri o benzyl beta galactopyranose; galactofuranoside derivative; pyranoside; unclassified drug; article; catalysis; chemical reaction kinetics; chemical structure; isotope labeling; nuclear magnetic resonance spectroscopy; reaction analysis; structure analysis; synthesis
Año:2000
Número:21
Página de inicio:3523
Página de fin:3525
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n21_p3523_Kovensky

Referencias:

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  • Besra, G.S., Khoo, K.-H., McNeil, M.R., Dell, A., Morris, H.R., Brennan, P.J., (1995) Biochemistry, 34, pp. 4257-4266
  • Previato, J.O., Gorin, P.A.J., Mazurek, M., Xavier, M.T., Fournet, B., Wieruszeski, J.M., Mendonca-Previato, L., (1990) J. Biol. Chem., 265, pp. 2518-2526
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  • Koplin, R., Brisson, J.R., Whitfield, C., (1997) J. Biol. Chem., 272, pp. 4121-4128
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  • Weston, A., Stern, R.J., Lee, R.L., Nassau, P.M., Monsey, D., Martin, S.L., Scherman, M.S., McNeil, M.R., (1997) Tuber. Lung Dis., 78, pp. 123-131
  • McMahon, S.A., Leonard, G.A., Buchanan, L.V., Giraud, M.-F., Naismith, J.H., (1999) Acta Crystallogr., D55, pp. 399-402
  • Lee, R.E., Smith, M.D., Pickering, L., Fleet, G.W.J., (1999) Tetrahedron Lett., 40, pp. 8689-8692
  • Kovensky, J., McNeil, M., Sinaÿ, P., (1999) J. Org. Chem., 64, pp. 6202-6205
  • Burton, A., Wyatt, P., Boons, G.-J., (1997) J. Chem. Soc., Perkin Trans. 1, pp. 2375-2382
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Citas:

---------- APA ----------
Kovensky, J. & Sinaÿ, P. (2000) . Synthesis of galactofuranosides by regioselective ring opening of a 1,4-anhydrogalactopyranose derivative: A possible chemical model for an unprecedented enzymatic reaction. European Journal of Organic Chemistry(21), 3523-3525.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n21_p3523_Kovensky [ ]
---------- CHICAGO ----------
Kovensky, J., Sinaÿ, P. "Synthesis of galactofuranosides by regioselective ring opening of a 1,4-anhydrogalactopyranose derivative: A possible chemical model for an unprecedented enzymatic reaction" . European Journal of Organic Chemistry, no. 21 (2000) : 3523-3525.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n21_p3523_Kovensky [ ]
---------- MLA ----------
Kovensky, J., Sinaÿ, P. "Synthesis of galactofuranosides by regioselective ring opening of a 1,4-anhydrogalactopyranose derivative: A possible chemical model for an unprecedented enzymatic reaction" . European Journal of Organic Chemistry, no. 21, 2000, pp. 3523-3525.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n21_p3523_Kovensky [ ]
---------- VANCOUVER ----------
Kovensky, J., Sinaÿ, P. Synthesis of galactofuranosides by regioselective ring opening of a 1,4-anhydrogalactopyranose derivative: A possible chemical model for an unprecedented enzymatic reaction. Eur. J. Org. Chem. 2000(21):3523-3525.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n21_p3523_Kovensky [ ]