Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

Anup Kumar Misra, Éva Bokor, Sándor Kun, Evelin Bolyog-Nagy, Ágnes Kathó, Ferenc Joó, László Somsák

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7 Citations (Scopus)

Abstract

[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixtures at 105 °C. O-Acetyl, O-benzoyl, and O-benzyl protecting groups, anomeric bromide and azide substituents as well as double bonds were shown to be compatible with these reaction conditions.

Original languageEnglish
Pages (from-to)5995-5998
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number44
DOIs
Publication statusPublished - Oct 28 2015

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Keywords

  • Amide
  • C-Glycoside
  • Nitrile
  • Ruthenium complex
  • Water

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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