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

  • Identification data

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

  • Others:

    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
    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: 2024-11-30
    Papper version: info:eu-repo/semantics/acceptedVersion
    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
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2017
    Publication Type: Journal Publications

  • Keywords:

    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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