Mostrar el registro sencillo del ítem
dc.contributor.author
Gola, Gabriel Francisco

dc.contributor.author
Tilve, Mariano Javier

dc.contributor.author
Gallo, Carola

dc.date.available
2019-01-29T14:45:06Z
dc.date.issued
2011-09
dc.identifier.citation
Gola, Gabriel Francisco; Tilve, Mariano Javier; Gallo, Carola; 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; Elsevier; Carbohydrate Research; 346; 12; 9-2011; 1495-1502
dc.identifier.issn
0008-6215
dc.identifier.uri
http://hdl.handle.net/11336/68841
dc.description.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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier

dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.subject
1,2-Cis
dc.subject
Diastereoselectivity
dc.subject
Galactofuranose
dc.subject
Glycosylation
dc.subject
Solvents Effects
dc.subject
Trichloroacetimidate
dc.subject.classification
Otras Ciencias Químicas

dc.subject.classification
Ciencias Químicas

dc.subject.classification
CIENCIAS NATURALES Y EXACTAS

dc.title
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
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2019-01-28T14:03:12Z
dc.journal.volume
346
dc.journal.number
12
dc.journal.pagination
1495-1502
dc.journal.pais
Países Bajos

dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Gola, Gabriel Francisco. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
dc.description.fil
Fil: Tilve, Mariano Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
dc.description.fil
Fil: Gallo, Carola. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
dc.journal.title
Carbohydrate Research

dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.carres.2011.04.005
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S000862151100173X
Archivos asociados