Abstract:
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-tert-butylsilylene-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. © 2016 American Chemical Society.
Registro:
Documento: |
Artículo
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Título: | Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives |
Autor: | Tilve, M.J.; Cori, C.R.; Gallo-Rodriguez, C. |
Filiación: | CIHIDECAR, Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, Buenos Aires, 1428, Argentina
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Palabras clave: | Oligosaccharides; Autocondensation; Glycosylation reactions; Hydroxyl groups; Innovative approaches; Regio-selective; Thioglycosides; Regioselectivity; disaccharide; furan derivative; galactose oligosaccharide; hydroxyl group; n acetylgalactosamine; oligosaccharide; thioglycoside; trisaccharide; acetylation; acylation; alkylation; Article; benzylation; carbohydrate synthesis; conformation; conformational transition; deacylation; glycosylation; ion transport; one pot synthesis; regioselectivity; ring opening; stereochemistry |
Año: | 2016
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Volumen: | 81
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Número: | 20
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Página de inicio: | 9585
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Página de fin: | 9594
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DOI: |
http://dx.doi.org/10.1021/acs.joc.6b01562 |
Título revista: | Journal of Organic Chemistry
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Título revista abreviado: | J. Org. Chem.
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ISSN: | 00223263
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CODEN: | JOCEA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n20_p9585_Tilve |
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Citas:
---------- APA ----------
Tilve, M.J., Cori, C.R. & Gallo-Rodriguez, C.
(2016)
. Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives. Journal of Organic Chemistry, 81(20), 9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562---------- CHICAGO ----------
Tilve, M.J., Cori, C.R., Gallo-Rodriguez, C.
"Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives"
. Journal of Organic Chemistry 81, no. 20
(2016) : 9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562---------- MLA ----------
Tilve, M.J., Cori, C.R., Gallo-Rodriguez, C.
"Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives"
. Journal of Organic Chemistry, vol. 81, no. 20, 2016, pp. 9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562---------- VANCOUVER ----------
Tilve, M.J., Cori, C.R., Gallo-Rodriguez, C. Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives. J. Org. Chem. 2016;81(20):9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562