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Abstract:

Glycosylation studies for the construction of 1,2-cis α-linkages with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including d-mannosyl and l-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH 2Cl2, Et2O, and acetonitrile as solvents. A non-participating solvent such as CH2Cl2 at -78 °C, favored the α-d-configuration. In contrast, acetonitrile strongly favored the β-d-configuration, whereas no selectivities were observed with Et 2O. The use of thiophene as an additive did not enhance the α-d-selectivity as in the pyranose counterpart. Although selectivities strongly depended on the acceptor, trichloroacetimidate 1 constitutes a valuable donor for the synthesis of α-d-Galf-(1→2)-l-Rha and α-d-Galf-(1→6)-d-Man. As these motifs are present in pathogenic microorganisms, these procedures described here are useful for the straightforward synthesis of natural oligosaccharides. © 2011 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation
Autor:Gola, G.; Tilve, M.J.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:1,2-Cis; Diastereoselectivity; Galactofuranose; Glycosylation; Solvents effects; Trichloroacetimidate; 1,2-Cis; Diastereo-selectivity; Galactofuranose; Glycosylations; Low temperatures; Pathogenic microorganisms; Pyranose; Trichloroacetimidate; Acetonitrile; Esterification; Glycosylation; Microorganisms; Solvents; Thiophene; Organic solvents; 2 o benzoyl 5,6 o isopropylidene d galactono 1,4 lactone; 3,4 di o benzyl alpha rhamnopyranoside; acetonitrile; lactone; methyl 2,3,4 tri o benzoyl alpha d mannopyranoside; methyl 2,3,4 tri o benzyl alpha d mannopyranoside; methyl 3 o benzoyl 4,6 o benzylidene alpha d mannopyranoside; o (2,3,5,6 tetra o benzyl beta d galactofuranosyl)trichloroacetimidate; oligosaccharide; pyranoside; solvent; thiophene; trichloroacetimidic acid; unclassified drug; article; glycosylation; low temperature procedures; priority journal; synthesis; Antigens, Bacterial; Antigens, Fungal; Bacteria; Chromatography, Thin Layer; Cold Temperature; Fungi; Furans; Glycoconjugates; Glycosylation; Magnetic Resonance Spectroscopy; Oligosaccharides; Solvents; Stereoisomerism; Trichloroacetic Acid; Tetra
Año:2011
Volumen:346
Número:12
Página de inicio:1495
Página de fin:1502
DOI: http://dx.doi.org/10.1016/j.carres.2011.04.005
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:acetonitrile, 75-05-8; lactone, 1338-03-0; thiophene, 110-02-1; Antigens, Bacterial; Antigens, Fungal; Furans; Glycoconjugates; Oligosaccharides; Solvents; Trichloroacetic Acid, 76-03-9; trichloroacetamide, 594-65-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n12_p1495_Gola

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Citas:

---------- APA ----------
Gola, G., Tilve, M.J. & Gallo-Rodriguez, C. (2011) . Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation. Carbohydrate Research, 346(12), 1495-1502.
http://dx.doi.org/10.1016/j.carres.2011.04.005
---------- CHICAGO ----------
Gola, G., Tilve, M.J., Gallo-Rodriguez, C. "Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation" . Carbohydrate Research 346, no. 12 (2011) : 1495-1502.
http://dx.doi.org/10.1016/j.carres.2011.04.005
---------- MLA ----------
Gola, G., Tilve, M.J., Gallo-Rodriguez, C. "Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation" . Carbohydrate Research, vol. 346, no. 12, 2011, pp. 1495-1502.
http://dx.doi.org/10.1016/j.carres.2011.04.005
---------- VANCOUVER ----------
Gola, G., Tilve, M.J., Gallo-Rodriguez, C. Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation. Carbohydr. Res. 2011;346(12):1495-1502.
http://dx.doi.org/10.1016/j.carres.2011.04.005