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dc.creatorGola, Gabriel Francisco-
dc.creatorTilve, Mariano Javier-
dc.creatorGallo, Carola-
dc.date2019-01-29T14:45:06Z-
dc.date2019-01-29T14:45:06Z-
dc.date2011-09-
dc.date2019-01-28T14:03:12Z-
dc.date.accessioned2019-04-29T15:56:06Z-
dc.date.available2019-04-29T15:56:06Z-
dc.identifierGola, 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.identifier0008-6215-
dc.identifierhttp://hdl.handle.net/11336/68841-
dc.identifierCONICET Digital-
dc.identifierCONICET-
dc.identifier.urihttp://rodna.bn.gov.ar:8080/jspui/handle/bnmm/305700-
dc.descriptionGlycosylation 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.descriptionFil: 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.descriptionFil: 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.descriptionFil: 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.formatapplication/pdf-
dc.formatapplication/pdf-
dc.languageeng-
dc.publisherElsevier-
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.carres.2011.04.005-
dc.relationinfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S000862151100173X-
dc.rightsinfo:eu-repo/semantics/restrictedAccess-
dc.rightshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/-
dc.sourcereponame:CONICET Digital (CONICET)-
dc.sourceinstname:Consejo Nacional de Investigaciones Científicas y Técnicas-
dc.sourceinstacron:CONICET-
dc.subject1,2-CIS-
dc.subjectDIASTEREOSELECTIVITY-
dc.subjectGALACTOFURANOSE-
dc.subjectGLYCOSYLATION-
dc.subjectSOLVENTS EFFECTS-
dc.subjectTRICHLOROACETIMIDATE-
dc.subjectOtras Ciencias Químicas-
dc.subjectCiencias Químicas-
dc.subjectCIENCIAS NATURALES Y EXACTAS-
dc.titleInfluence 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.typeinfo:eu-repo/semantics/article-
dc.typeinfo:eu-repo/semantics/publishedVersion-
dc.typeinfo:ar-repo/semantics/articulo-
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