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Metal-free and VOC-free Synthesis of O-Glycosides in Supercritical CO2

  • Datos identificativos

    Identificador: PC:3121
    Autores:
    Castillón, S.Cardona, A.Boutureira, O.Díaz, Y.Matheu, M. I.
    Resumen:
    Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylations in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology here described can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and showed to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.
  • Otros:

    Autor según el artículo: Castillón, S. ; Cardona, A. ; Boutureira, O.; Díaz, Y. ; Matheu, M. I.
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: CASTILLÓN MIRANDA, SERGIO; Cardona, A. ; Boutureira, O.; DÍAZ GIMÉNEZ, MARÍA YOLANDA; MATHEU MALPARTIDA, MARÍA ISABEL
    Palabras clave: Supercritial CO2 glycosylation
    Resumen: Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylations in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology here described can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and showed to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.
    Grupo de investigación: Síntesis Orgànica Estereoselectiva
    Áreas temáticas: Chemistry Química Química
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1463-9262
    Identificador del autor: 0000-0002-0690-7549; ; ; 0000-0001-5567-8108; 0000-0001-5216-9260
    Fecha de alta del registro: 2018-02-27
    Volumen de revista: 19
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://pubs.rsc.org/en/content/articlelanding/2017/gc/c7gc00722a#!divAbstract
    Programa de financiación: plan; RYC-2015-17705 plan; Excelencia; CTQ2014-58664-R
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.1039/c7gc00722a
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2017
    Página inicial: 2687
    Tipo de publicación: Article Artículo Article
  • Palabras clave:

    Punt crític
    Glicols
    Supercritial CO2
    glycosylation
    Chemistry
    Química
    Química
    1463-9262
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