Articles producció científica> Química Analítica i Química Orgànica

Oxidative activation of C-S bonds with an electropositive nitrogen promoter enables orthogonal glycosylation of alkyl over phenyl thioglycosides

  • Dades identificatives

    Identificador: imarina:6040629
    Handle: https://hdl.handle.net/20.500.11797/imarina6040629
    Autors:
    Kitowski, AnnabelJimenez-Moreno, EsterSalvado, MiriamMestre, JordiCastillon, SergioJimenez-Oses, GonzaloBoutureira, OmarBemardes, Gonzalo J L
    Resum:
    © 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.

  • Altres:

    Autor segons l'article: Kitowski, Annabel; Jimenez-Moreno, Ester; Salvado, Miriam; Mestre, Jordi; Castillon, Sergio; Jimenez-Oses, Gonzalo; Boutureira, Omar; Bemardes, Gonzalo J L
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Boutureira Martín, Omar / Castillón Miranda, Sergio / Mestre Ventura, Jordi / Salvadó Artells, Marçal
    Paraules clau: Armed-disarmed concept platform oligosaccharide synthesis mechanisms glycosides donors couplings configuration active-latent
    Resum: © 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: omar.boutureira@urv.cat m.salvado@urv.cat sergio.castillon@urv.cat
    Identificador de l'autor: 0000-0002-0768-8309 0000-0002-9399-6649 0000-0002-0690-7549
    Data d'alta del registre: 2024-11-30
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Organic Letters. 19 (19): 5490-5493
    Referència de l'ítem segons les normes 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
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2017
    Tipus de publicació: Journal Publications

  • Paraules clau:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Armed-disarmed concept
    platform
    oligosaccharide synthesis
    mechanisms
    glycosides
    donors
    couplings
    configuration
    active-latent
    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

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