Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions

Ian J. Talisman, Vineet Kumar, Jeffrey R. Deschamps, Mark Frisch, Sanjay V. Malhotra

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl) imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the β isomer regardless of neighboring group effects.

Original languageEnglish (US)
Pages (from-to)2337-2341
Number of pages5
JournalCarbohydrate Research
Volume346
Issue number15
DOIs
StatePublished - Nov 8 2011
Externally publishedYes

Keywords

  • Carbohydrates
  • O-Glycosidation
  • Silver N-heterocyclic carbene complex

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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