Articles producció científica> Química Analítica i Química Orgànica

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

  • Dades identificatives

    Identificador: PC:3121
    Autors:
    Castillón, S.Cardona, A.Boutureira, O.Díaz, Y.Matheu, M. I.
    Resum:
    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.
  • Altres:

    Autor segons l'article: Castillón, S. ; Cardona, A. ; Boutureira, O.; Díaz, Y. ; Matheu, M. I.
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: CASTILLÓN MIRANDA, SERGIO; Cardona, A. ; Boutureira, O.; DÍAZ GIMÉNEZ, MARÍA YOLANDA; MATHEU MALPARTIDA, MARÍA ISABEL
    Paraules clau: Supercritial CO2 glycosylation
    Resum: 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.
    Grup de recerca: Síntesis Orgànica Estereoselectiva
    Àrees temàtiques: Chemistry Química Química
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1463-9262
    Identificador de l'autor: 0000-0002-0690-7549; ; ; 0000-0001-5567-8108; 0000-0001-5216-9260
    Data d'alta del registre: 2018-02-27
    Volum de revista: 19
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.rsc.org/en/content/articlelanding/2017/gc/c7gc00722a#!divAbstract
    Programa de finançament: plan; RYC-2015-17705 plan; Excelencia; CTQ2014-58664-R
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1039/c7gc00722a
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2017
    Pàgina inicial: 2687
    Tipus de publicació: Article Artículo Article
  • Paraules clau:

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