Author, as appears in the article.: Kitowski, Annabel; Jimenez-Moreno, Ester; Salvado, Miriam; Mestre, Jordi; Castillon, Sergio; Jimenez-Oses, Gonzalo; Boutureira, Omar; Bemardes, Gonzalo J L; Bemardes, Gonzalo J L
Department: Química Analítica i Química Orgànica
URV's Author/s: Boutureira Martín, Omar / Castillón Miranda, Sergio / Mestre Ventura, Jordi / Salvadó Artells, Marçal
Keywords: Armed-disarmed concept platform oligosaccharide synthesis mechanisms glycosides donors couplings configuration active-latent
Abstract: © 2017 American Chemical Society. A method for the selective activation of thioglycosides that uses the N+-thiophilic reagent Omesitylenesulfonylhydroxylamine (MSH) as a promoter is presented. The reaction proceeds via anomeric mesitylensulfonate intermediates, which could be isolated and fully characterized by placing a fluorine atom at the C2 position. In the presence of a soft Lewis acid, glycosylation reaction proceeds at ambient temperature with good yields. It is further demonstrated that it is possible to orthogonally activate S-ethyl in the presence of S-phenyl donors, enabling the design of sequential glycosylation strategies.
Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: omar.boutureira@urv.cat m.salvado@urv.cat sergio.castillon@urv.cat
Author identifier: 0000-0002-0768-8309 0000-0002-9399-6649 0000-0002-0690-7549
Record's date: 2024-09-28
Papper version: info:eu-repo/semantics/acceptedVersion
Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.7b02886
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Organic Letters. 19 (19): 5490-5493
APA: Kitowski, Annabel; Jimenez-Moreno, Ester; Salvado, Miriam; Mestre, Jordi; Castillon, Sergio; Jimenez-Oses, Gonzalo; Boutureira, Omar; Bemardes, Gonzal (2017). Oxidative activation of C-S bonds with an electropositive nitrogen promoter enables orthogonal glycosylation of alkyl over phenyl thioglycosides. Organic Letters, 19(19), 5490-5493. DOI: 10.1021/acs.orglett.7b02886
Article's DOI: 10.1021/acs.orglett.7b02886
Entity: Universitat Rovira i Virgili
Journal publication year: 2017
Publication Type: Journal Publications
Repositori URV