Abstract:
The synthesis of 2,3,5,6-tetra-O-benzyl-D-galactofuranose, a useful compound for α-glycosylation studies, is described. Direct anomeric O-alkylation of galactose was employed for alpha-allylation to yield pure allyl α-D-galactofuranoside, which is a versatile precursor for the synthesis of galactofuranose-containing oligosaccharides. Allyl removal of the benzylated galactofuranosyl derivative was performed using palladium (II) chloride as catalyst. ©ARKAT.
Registro:
Documento: |
Artículo
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Título: | Synthesis of 2,3,5,6-tetra-O-benzyl-D-galactofuranose for α-glycosidation |
Autor: | Gola, G.; Libenson, P.; Gandolfi-Donadío, L.; Gallo-Rodriguez, C. |
Filiación: | CIHIDECAR, Departamento de Química Orgánica, Pabellón II, 1428 Buenos Aires, Argentina
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Palabras clave: | α-Galactofuranosyl; 1,2-cis-glycosylation; Allyl galactofuranoside; Galactofuranose |
Año: | 2006
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Volumen: | 2005
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Número: | 12
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Página de inicio: | 234
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Página de fin: | 242
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Título revista: | Arkivoc
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Título revista abreviado: | Arkivoc
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ISSN: | 14246376
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PDF: | https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2005_n12_p234_Gola.pdf |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p234_Gola |
Referencias:
- Lederkremer, R.M., Gallo-Rodriguez, C., (2004) Adv. Carbohydr. Chem. Biochem., 59, p. 9
- Lindberg, B., (1990) Adv. Carbohydr. Chem. Biochem., 48, p. 279
- Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, p. 547
- Notermans, S., Veeneman, G.H., Van Zuylen, C.W.E.M., Hoogerhout, P., Van Boom, J.H., (1988) Mol. Immunol., 25, p. 975
- Pedersen, L.L., Turco, S.J., (2003) Cell. Mol. Life Sci, 60, p. 259
- Sanders, D.A.R., Staines, A.G., McMahon, S.A., McNeil, M.R., Whitfield, C., Naismith, J.H., (2001) Nat. Struct. Biol., 8, p. 858
- Kremer, L., Dover, L.G., Morehouse, C., Hitchin, P., Everett, M., Morris, H.R., Dell, A., Besra, G.S., (2001) J. Biol. Chem., 276, p. 26430
- Crick, D.C., Mahaprata, S., Brennan, P.J., (2001) Glycobiology, 11, p. 107
- Turco, S.J., Descoteaux, A., (1992) Annu. Rev. Microbiol., 46, p. 65
- Jones, C., Todeschini, A.R., Agrellos, O.A., Previato, J.O., Mendonca-Previato, L., (2004) Biochemistry, 43, p. 11889
- Gerwig, G.J., De Waard, P., Kamerling, J.P., Vliegenthart, J.F.G., Morgenstern, E., Lamed, R., Bayer, E.A., (1989) J. Biol. Chem., 264, p. 1027
- Gerwig, G.J., Kamerling, J.P., Vliegenthart, J.F.G., Morag, E., Lamed, R., Bayer, E.A., (1993) J. Biol. Chem., 268, p. 26956
- (1992) Eur. J. Biochem., 205, p. 799
- Richards, J.C., Perry, M.B., Kniskern, P.J., (1988) Can. J. Chem., 67, p. 1038
- Linnerborg, M., Wollin, R., Wildmalm, G., (1997) Eur. J. Biochem., 246, p. 565
- Jansson, P.E., Lindberg, B., (1980) Carbohydr. Res., 82, p. 97
- Kogan, G., Matulová, M., Michalková, E., (2002) Z. Naturfosch., 57 C, p. 452
- Parra, E., Jiménez-Barbero, J., Bernabé, M., Leal, J.A., Prieto, A., Gomez-Miranda, B., (1994) Carbohydr. Res., 251, p. 315
- Ahrazem, O., Prieto, A., San-Blas, G., Leal, J.A., Jimenez-Barbero, J., Bernabé, M., (2003) Glycobiology, 13, p. 743
- Lowary, T.L., (2003) Curr. Opinion Chem. Biol., 7, p. 749
- Demchenko, A.V., (2003) Curr. Org. Chem., 7, p. 35
- Arasappan, A., Fraser-Reid, B., (1995) Tetrahedron Lett., 36, p. 7967
- Guelin, M., Ferrieres, V., Plusquellec, D., (1997) Carbohydr. Lett., 2, p. 381
- Guelin, M., Ferrieres, V., Plusquellec, D., (2000) Eur. J. Org. Chem., p. 1423
- Fraser-Reid, B., López, J.C., Gómez, A.M., Uriel, C., (2004) Eur. J. Org. Chem., p. 1387
- Schmidt, R.R., Jung, K.-H., (1997) Preparative Carbohydrate Chemistry, pp. 283-312. , Hanessian, S., Ed.; Marcel Dekker
- Gallo-Rodriguez, C., Gandolfi, L., Lederkremer, R.M., (1999) Org. Lett., 1, p. 245
- Gallo-Rodriguez, C., Gil Libarona, M.A., Mendoza, V.M., Lederkremer, R.M., (2002) Tetrahedron, 58, p. 9373
- Gandolfi-Donadio, L., Gallo-Rodriguez, C., Lederkremer, R.M., (2002) J. Org. Chem., 67, p. 4430
- Gandolfi-Donadio, L., Gallo-Rodriguez, C., Lederkremer, R.M., (2003) J. Org. Chem., 68, p. 6928
- Decoster, E., Lacombe, J.-M., Strebler, J.-L., Ferrari, B., Pavia, A.A., (1983) J. Carbohydr. Chem., 2, p. 329
- Kovensky, J., McNeil, M., Sinay, P., (1999) J. Org. Chem., 64, p. 6202
- Klotz, W., Schmidt, R.R., (1993) Liebigs Ann. Chem., p. 683
- Guelin, M., Ferrieres, V., Lefeuvre, M., Plusquellec, D., (2003) Eur. J. Org. Chem., p. 1285
Citas:
---------- APA ----------
Gola, G., Libenson, P., Gandolfi-Donadío, L. & Gallo-Rodriguez, C.
(2006)
. Synthesis of 2,3,5,6-tetra-O-benzyl-D-galactofuranose for α-glycosidation. Arkivoc, 2005(12), 234-242.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p234_Gola [ ]
---------- CHICAGO ----------
Gola, G., Libenson, P., Gandolfi-Donadío, L., Gallo-Rodriguez, C.
"Synthesis of 2,3,5,6-tetra-O-benzyl-D-galactofuranose for α-glycosidation"
. Arkivoc 2005, no. 12
(2006) : 234-242.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p234_Gola [ ]
---------- MLA ----------
Gola, G., Libenson, P., Gandolfi-Donadío, L., Gallo-Rodriguez, C.
"Synthesis of 2,3,5,6-tetra-O-benzyl-D-galactofuranose for α-glycosidation"
. Arkivoc, vol. 2005, no. 12, 2006, pp. 234-242.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p234_Gola [ ]
---------- VANCOUVER ----------
Gola, G., Libenson, P., Gandolfi-Donadío, L., Gallo-Rodriguez, C. Synthesis of 2,3,5,6-tetra-O-benzyl-D-galactofuranose for α-glycosidation. Arkivoc. 2006;2005(12):234-242.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p234_Gola [ ]