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Artículo

Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene-d-galactofuranosides. Synthesis of (1→5)-β-d-Galactofuranosyl Derivatives

Tilve, Mariano JavierIcon ; Cori Calizaya, Carmen RosaIcon ; Gallo, CarolaIcon
Fecha de publicación: 09/2016
Editorial: American Chemical Society
Revista: Journal Of Organic Chemistry
ISSN: 0022-3263
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

The use of thiogalactofuranoside as donors for the construction of internal Galf containing oligosaccharide is limited, probably due to the difficulty to functionalize thiogalactofuranoside derivatives showing O-2, O-3, and O-5 with similar reactivity. An efficient method for complete regioselective 5-O-opening of conformationally restricted 3,5-O-di-tertbutylsilylene-D-galactofuranoside derivatives was developed. The use of a solution nBu4NF (1.1 equiv) in CH2Cl2 on 6 gave the 5-OH free derivative 10 as the only product (90%). 3-O-Di-tert-butylhydroxysilyl derivative 10 was stable upon purification and glycosylation reaction. Preactivation of conformationally restricted thioglycoside 6 employing p-NO2-benzensulfenyl chloride/AgOTf followed by condensation over the 5-OH thioglycoside acceptor 10 gave the corresponding disaccharide 12 without autocondensation byproduct. Regioselective 5-O-deprotection was also successfully performed over the (1→5)-β-D-galactofuranosyl di- and trisaccharide derivatives 12 and 13. This methodology allowed the differentiation between the secondary hydroxyl groups OH-3 and OH-5 of 1,2-cis or 1,2-trans D-galactofuranoside derivatives, and it still constitutes an innovative approach to access oligosaccharides of pharmacological importance.
Palabras clave: Glycosylation , Regioselective , Tioglycoside , Galactofuranoside
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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/17726
DOI: http://dx.doi.org/10.1021/acs.joc.6b01562
URL: http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01562
Colecciones
Articulos(CIHIDECAR)
Articulos de CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Citación
Tilve, Mariano Javier; Cori Calizaya, Carmen Rosa; Gallo, Carola; Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene-d-galactofuranosides. Synthesis of (1→5)-β-d-Galactofuranosyl Derivatives; American Chemical Society; Journal Of Organic Chemistry; 81; 20; 9-2016; 9585-9594
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