Autor según el artículo: Kitowski A; Jiménez-Moreno E; Salvadó M; Mestre J; Castillón S; Jiménez-Osés G; Boutureira O; Bernardes G
Departamento: Química Analítica i Química Orgànica
Autor/es de la URV: Boutureira Martín, Omar / Castillón Miranda, Sergio
Palabras clave: Armed-disarmed concept platform oligosaccharide synthesis mechanisms glycosides donors couplings configuration active-latent
Resumen: © 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.
Áreas temáticas: 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
Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
Direcció de correo del autor: sergio.castillon@urv.cat omar.boutureira@urv.cat
Identificador del autor: 0000-0002-0690-7549 0000-0002-0768-8309
Fecha de alta del registro: 2023-11-18
Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acs.orglett.7b02886
Referencia al articulo segun fuente origial: Organic Letters. 19 (19): 5490-5493
Referencia de l'ítem segons les normes APA: Kitowski A; Jiménez-Moreno E; Salvadó M; Mestre J; Castillón S; Jiménez-Osés G; Boutureira O; Bernardes G (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
URL Documento de licencia: http://repositori.urv.cat/ca/proteccio-de-dades/
DOI del artículo: 10.1021/acs.orglett.7b02886
Entidad: Universitat Rovira i Virgili
Año de publicación de la revista: 2017
Tipo de publicación: Journal Publications
Repositori URV