Autor segons l'article: Mestre, Jordi; Bascuas, Isabel; Bernus, Miguel; Castillon, Sergio; Boutureira, Omar
Departament: Química Analítica i Química Orgànica
Autor/s de la URV: Bascuas Jiménez De Bagües, Isabel / Bernús Pérez, Miguel / Boutureira Martín, Omar / Castillón Miranda, Sergio / Mestre Ventura, Jordi
Paraules clau: Thioglycosides Stereocontrolled synthesis Probes Molecular recognition Mechanisms Glycosidation Glycals Fluorine Enables Chemical glycosylation
Resum: 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.
Àrees temàtiques: Organic chemistry Chemistry, organic
Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
Adreça de correu electrònic de l'autor: miguel.bernus@urv.cat isabel.bascuas@estudiants.urv.cat isabel.bascuas@estudiants.urv.cat omar.boutureira@urv.cat miguel.bernus@urv.cat miguel.bernus@urv.cat sergio.castillon@urv.cat
Identificador de l'autor: 0000-0003-0302-0720 0000-0002-0768-8309 0000-0003-0302-0720 0000-0003-0302-0720 0000-0002-0690-7549
Data d'alta del registre: 2024-11-30
Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
Referència a l'article segons font original: Organic Chemistry Frontiers. 10 (10): 2405-2415
Referència de l'ítem segons les normes APA: Mestre, Jordi; Bascuas, Isabel; Bernus, Miguel; Castillon, Sergio; Boutureira, Omar (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
Entitat: Universitat Rovira i Virgili
Any de publicació de la revista: 2023
Tipus de publicació: Journal Publications
Repositori URV