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

  1. Author:
    Talisman, I. J.
    Kumar, V.
    Deschamps, J. R.
    Frisch, M.
    Malhotra, S. V.

  2. Author Address

    [Talisman, IJ; Kumar, V; Malhotra, SV] NCI, Lab Synthet Chem, SAIC Frederick Inc, Frederick, MD 21702 USA. [Deschamps, JR; Frisch, M] USN, Res Lab, Washington, DC 20375 USA.;Malhotra, SV (reprint author), NCI, Lab Synthet Chem, SAIC Frederick Inc, 1050 Boyles St, Frederick, MD 21702 USA;malhotrasa@mail.nih.gov
    1. Year: 2011
    2. Date: Nov
  2. Journal: Carbohydrate Research
    1. 346
    2. 15
    3. Pages: 2337-2341
  4. Type of Article: Article
  5. ISSN: 0008-6215
  1. 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 13 isomer regardless of neighboring group effects. (C) 2011 Elsevier Ltd. All rights reserved.

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External Sources

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  2. DOI: 10.1016/j.carres.2011.07.025
  3. View record in Web of Science®
  4. WOS: 000296950400003

Library Notes

  1. Fiscal Year: FY2011-2012
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