Artículo
Gallo-Rodriguez, C.; Gandolfi, L.; De Lederkremer, R.M. "Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation" (1999) Organic Letters. 1(2):245-247
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Abstract:
(equation presented) In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. β-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step. The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside (11) with penta-O-benzoyl-α,β-D-galactofuranose (4) gave the derivative of β-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.
Registro:
| Documento: | Artículo |
| Título: | Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation |
| Autor: | Gallo-Rodriguez, C.; Gandolfi, L.; De Lederkremer, R.M. |
| Filiación: | Depto. de Quim. Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires 1428, Argentina |
| Palabras clave: | disaccharide; galactofuranosyl 1 3 N acetylglucosamine; galactofuranosyl 1 6 N acetylglucosamine; galactofuranosyl-1-3-N-acetylglucosamine; galactofuranosyl-1-6-N-acetylglucosamine; mucin; stannic chloride; tin derivative; animal; article; catalysis; chemistry; glycosylation; synthesis; Trypanosoma cruzi; Animals; Catalysis; Disaccharides; Glycosylation; Mucins; Tin Compounds; Trypanosoma cruzi |
| Año: | 1999 |
| Volumen: | 1 |
| Número: | 2 |
| Página de inicio: | 245 |
| Página de fin: | 247 |
| Título revista: | Organic Letters |
| Título revista abreviado: | Org. Lett. |
| ISSN: | 15237060 |
| CAS: | Disaccharides; galactofuranosyl-1-3-N-acetylglucosamine; galactofuranosyl-1-6-N-acetylglucosamine; Mucins; stannic chloride, 7646-78-8; Tin Compounds |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez |
Referencias:
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- Gallo-Rodriguez, C., Varela, O., De Lederkremer, R.M., (1996) J. Org. Chem., 61, p. 1886
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- Schmidt, R.R., (1996) Modern Methods in Carbohydrate Synthesis, p. 20. , Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam
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- Choudhury, A.K., Roy, N., (1998) Carbohydr. Res., 308, p. 207
- Marino, C., Varela, O., De Lederkremer, R.M., (1989) Carbohydr. Res., 190, p. 65
- De Lederkremer, R.M., Marino, C., Varela, O., (1990) Carbohydr. Res., 200, p. 227
- Gallo-Rodriguez, C., Varela, O., De Lederkremer, R.M., (1998) Carbohydr. Res., 305, p. 163
- Allen, P.Z., (1962) Methods in Carbohydrate Chemistry, 1, p. 372. , Whistler, R. L. Wolfrom, M. L., Eds.; Academic Press: New York
- note; note; note
Citas:
---------- APA ----------
Gallo-Rodriguez, C., Gandolfi, L. & De Lederkremer, R.M. (1999) . Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation. Organic Letters, 1(2), 245-247.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez [ ]
---------- CHICAGO ----------
Gallo-Rodriguez, C., Gandolfi, L., De Lederkremer, R.M. "Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation" . Organic Letters 1, no. 2 (1999) : 245-247.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez [ ]
---------- MLA ----------
Gallo-Rodriguez, C., Gandolfi, L., De Lederkremer, R.M. "Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation" . Organic Letters, vol. 1, no. 2, 1999, pp. 245-247.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez [ ]
---------- VANCOUVER ----------
Gallo-Rodriguez, C., Gandolfi, L., De Lederkremer, R.M. Synthesis of β-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of β-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation. Org. Lett. 1999;1(2):245-247.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v1_n2_p245_GalloRodriguez [ ]
