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

  1. Kitowski, A. 34
  2. Jiménez-Moreno, E. 3
  3. Salvadó, M. 13
  4. Mestre, J. 1
  5. Castillón, S. 1
  6. Jiménez-Osés, G. 2
  7. Boutureira, O. 1
  8. Bernardes, G.J.L. 34
  1. 1 Universitat Rovira i Virgili
    info

    Universitat Rovira i Virgili

    Tarragona, España

    ROR https://ror.org/00g5sqv46

  2. 2 Universidad de La Rioja
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    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  3. 3 University of Cambridge
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    University of Cambridge

    Cambridge, Reino Unido

    ROR https://ror.org/013meh722

  4. 4 Universidade de Lisboa
    info

    Universidade de Lisboa

    Lisboa, Portugal

    ROR https://ror.org/01c27hj86

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Revista:
Organic Letters

ISSN: 1523-7060

Año de publicación: 2017

Volumen: 19

Número: 19

Páginas: 5490-5493

Tipo: Artículo

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DOI: 10.1021/ACS.ORGLETT.7B02886 SCOPUS: 2-s2.0-85032701747 WoS: WOS:000412789600123 GOOGLE SCHOLAR

Otras publicaciones en: Organic Letters

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Financiación Adicional RAMÓN Y CAJAL G.J.O.

2015/00062/001

Resumen

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. © 2017 American Chemical Society.