Autor según el artículo: Mestre, J; Bascuas, I; Bernús, M; Castillón, S; Boutureira, O
Departamento: Química Analítica i Química Orgànica
Autor/es de la URV: Bascuas Jiménez De Bagües, Isabel / Bernús Pérez, Miguel / Boutureira Martín, Omar / Castillón Miranda, Sergio / Mestre Ventura, Jordi
Palabras clave: Thioglycosides Stereocontrolled synthesis Probes Molecular recognition Mechanisms Glycosidation Glycals Fluorine Enables Chemical glycosylation
Resumen: Fluorinated carbohydrate mimetics are valuable molecular fragments in contemporary Glycoscience. Available synthetic protocols are mainly restricted to the preparation of 'standard' monofluorinated derivatives, whereas their more complex C(sp(3))-CF3 congeners remain virtually underdeveloped. A protocol for accessing a series of previously uncharted 2-deoxy-2-trifluoromethyl-d-hexopyranosides from d-glycals is disclosed. The stereoselectivity of the glycosylation step, which is mainly governed by a combination of electronic and more dominant steric factors, revealed a pronounced substrate control rendering 1,2-trans glycosides as a result of the configuration of the CF3 moiety at C-2. The synthetic utility of this approach was demonstrated in the preparation of 2-CF3-glycoconjugates of natural origin, including disaccharides, cholesterol analogs, amino acids, and sphingosine/phytosphingosine derivatives.
Áreas temáticas: Organic chemistry Chemistry, organic
Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
Direcció de correo del autor: miguel.bernus@urv.cat sergio.castillon@urv.cat miguel.bernus@urv.cat miguel.bernus@urv.cat omar.boutureira@urv.cat isabel.bascuas@estudiants.urv.cat isabel.bascuas@estudiants.urv.cat
Identificador del autor: 0000-0003-0302-0720 0000-0002-0690-7549 0000-0003-0302-0720 0000-0003-0302-0720 0000-0002-0768-8309
Fecha de alta del registro: 2024-04-06
Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
Enlace a la fuente original: https://pubs.rsc.org/en/content/articlelanding/2023/qo/d3qo00274h
URL Documento de licencia: http://repositori.urv.cat/ca/proteccio-de-dades/
Referencia al articulo segun fuente origial: Organic Chemistry Frontiers. 10 (10): 2405-2415
Referencia de l'ítem segons les normes APA: Mestre, J; Bascuas, I; Bernús, M; Castillón, S; Boutureira, O (2023). Stereoselective access to 2-deoxy-2-trifluoromethyl sugar mimetics by trifluoromethyl-directed 1,2-trans glycosylation. Organic Chemistry Frontiers, 10(10), 2405-2415. DOI: 10.1039/d3qo00274h
DOI del artículo: 10.1039/d3qo00274h
Entidad: Universitat Rovira i Virgili
Año de publicación de la revista: 2023
Tipo de publicación: Journal Publications
Repositori URV