Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Sandra Medina, Matthew J. Harper, Edward I. Balmond, Silvia Miranda, Giacomo Crisenza, Diane M. Coe, Eoghan M. McGarrigle, M. Carmen Galan

Research output: Contribution to journalArticlepeer-review

Abstract

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.
Original languageEnglish
Pages (from-to)4222–4225
Number of pages4
JournalOrganic Letters
Volume18
Issue number17
DOIs
Publication statusPublished - 16 Aug 2016

Keywords

  • Carbohydrates
  • Catalysts
  • Peptides and proteins
  • Post-translational modification
  • Substitution Reactions

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