Author, as appears in the article.: Mestre, J; Bascuas, I; Bernús, M; Castillón, S; Boutureira, O
Department: Química Analítica i Química Orgànica
URV's Author/s: Bascuas Jiménez De Bagües, Isabel / Bernús Pérez, Miguel / Boutureira Martín, Omar / Castillón Miranda, Sergio / Mestre Ventura, Jordi
Keywords: Thioglycosides Stereocontrolled synthesis Probes Molecular recognition Mechanisms Glycosidation Glycals Fluorine Enables Chemical glycosylation
Abstract: 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.
Thematic Areas: Organic chemistry Chemistry, organic
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: 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
Author identifier: 0000-0003-0302-0720 0000-0002-0768-8309 0000-0003-0302-0720 0000-0003-0302-0720 0000-0002-0690-7549
Record's date: 2024-08-03
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2023/qo/d3qo00274h
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Organic Chemistry Frontiers. 10 (10): 2405-2415
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
Article's DOI: 10.1039/d3qo00274h
Entity: Universitat Rovira i Virgili
Journal publication year: 2023
Publication Type: Journal Publications
Repositori URV