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Abstract:

A conformationally restricted 2-O-benzyl-3,5-O-di-tert-butylsilylene- β-d-thiogalactofuranoside donor was prepared from benzyl α-d-galactofuranoside and its donor capability was studied for stereoselective 1,2-cis α-d-galactofuranosylation. An unusual chemical behavior in benzylation and hydrogenolysis reactions was observed after the introduction of the 3,5-O-di-tert-butylsilylene protecting group into the galactofuranosyl moiety. The influence of the solvent, temperature, and activating system was evaluated. The NIS/AgOTf system, widely used in 1,2-cis β-arabinofuranosylation, was not satisfactory enough for 1,2-cis galactofuranosylation. However, moderate to high α-selectivity was obtained with all the acceptors employed when using p-NO2PhSCl/AgOTf as a promoting system, in CH2Cl2 at -78 °C. The order of the addition of the reactants (premixing or preactivation) did not affect substantially the stereochemical course of the glycosylation reaction. The α-d-Galf-(1→6)-d-Man linkage was achieved with complete diastereoselectivity by preactivation of the conformationally constrained thioglycoside donor. © 2014 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Conformationally restricted 3,5-O-(di-tert-butylsilylene)-d- galactofuranosyl thioglycoside donor for 1,2-cis α-d-galactofuranosylation
Autor: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; Galactofuranose; Glycosylation; Protecting groups; Solvents effects; Thioglycoside; Glycosylation; Stereoselectivity; 1,2-cis; Chemical behavior; Diastereo-selectivity; Galactofuranose; Glycosylation reactions; Hydrogenolysis reactions; Protecting group; Thioglycosides; Esterification; Glycosylation; 4 tolyl 6 o acetyl 2 o benzyl 3,5 o (di tert butylsilanediyl) 1 thiol beta dextro galactofuranoside; cyclohexanol; solvent; thioglycoside; unclassified drug; 3,5-O-di-tert-butylsilylene-beta-D-thiogalactofuranoside; butane; di-tert-butylsilylene; silane derivative; thioglycoside; acetylation; article; benzylation; carbon nuclear magnetic resonance; chemical modification; conformation; galactofuranosylation; glycosylation; hydrogen bond; hydrogenolysis; nonhuman; priority journal; proton nuclear magnetic resonance; stereochemistry; synthesis; Talaromyces flavus; temperature; thin layer chromatography; Trypanosoma cruzi; chemistry; conformation; glycosylation; stereoisomerism; Article; carbohydrate synthesis; column chromatography; controlled study; heteronuclear single quantum coherence; low temperature; nucleophilicity; precursor; purification; Butanes; Carbohydrate Conformation; Chemistry Techniques, Synthetic; Glycosylation; Silanes; Solvents; Stereoisomerism; Thiogalactosides; Thioglycosides
Año:2014
Volumen:397
Página de inicio:7
Página de fin:17
DOI: http://dx.doi.org/10.1016/j.carres.2014.07.024
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:cyclohexanol, 108-93-0; butane, 106-97-8; 3,5-O-di-tert-butylsilylene-beta-D-thiogalactofuranoside; Butanes; di-tert-butylsilylene; Silanes; Solvents; Thiogalactosides; Thioglycosides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v397_n_p7_Tilve

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Citas:

---------- APA ----------
Tilve, M.J. & Gallo-Rodriguez, C. (2014) . Conformationally restricted 3,5-O-(di-tert-butylsilylene)-d- galactofuranosyl thioglycoside donor for 1,2-cis α-d-galactofuranosylation. Carbohydrate Research, 397, 7-17.
http://dx.doi.org/10.1016/j.carres.2014.07.024
---------- CHICAGO ----------
Tilve, M.J., Gallo-Rodriguez, C. "Conformationally restricted 3,5-O-(di-tert-butylsilylene)-d- galactofuranosyl thioglycoside donor for 1,2-cis α-d-galactofuranosylation" . Carbohydrate Research 397 (2014) : 7-17.
http://dx.doi.org/10.1016/j.carres.2014.07.024
---------- MLA ----------
Tilve, M.J., Gallo-Rodriguez, C. "Conformationally restricted 3,5-O-(di-tert-butylsilylene)-d- galactofuranosyl thioglycoside donor for 1,2-cis α-d-galactofuranosylation" . Carbohydrate Research, vol. 397, 2014, pp. 7-17.
http://dx.doi.org/10.1016/j.carres.2014.07.024
---------- VANCOUVER ----------
Tilve, M.J., Gallo-Rodriguez, C. Conformationally restricted 3,5-O-(di-tert-butylsilylene)-d- galactofuranosyl thioglycoside donor for 1,2-cis α-d-galactofuranosylation. Carbohydr. Res. 2014;397:7-17.
http://dx.doi.org/10.1016/j.carres.2014.07.024