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Application of Halide Molten Salts as Novel Reaction Media for O-Glycosidic Bond Formation

  1. Author:
    Kumar, V.
    Talisman, I. J.
    Malhotra, S. V.

  2. Author Address

    [Kumar, Vineet; Talisman, Ian Jamie; Malhotra, Sanjay V.] NCI, Lab Synthet Chem, SAIC Frederick Inc, Frederick, MD 21702 USA.;Malhotra, SV, NCI, Lab Synthet Chem, SAIC Frederick Inc, 1050 Boyles St, Frederick, MD 21702 USA.;malhotrasa@mail.nih.gov
    1. Year: 2010
    2. Date: Jun
  2. Journal: European Journal of Organic Chemistry
    1. 18
    2. Pages: 3377-3381
  4. Type of Article: Article
  5. ISSN: 1434-193X
  1. Abstract:

    In this study we have explored the application of halide molten salts as reaction media for O-glycosidic bond formation under basic conditions and mild heating. Eighteen different room-temperature ionic liquids and molten salts, representing four different classes of cations (i.e. imidazolium, pyridinium, pyrrolidinium and ammonium), were screened in the glycosidation reaction of p-nitrophenol with aceto-bromo-alpha-D-galactose. 1-Butyl-4-methylimidazolium chloride (BMIM center dot Cl) gave the best results and was applied in the reactions of other phenolic substrates to give the products with up to 80% yields. All the reactions were highly selective to give the beta-anomers, and the molten salt BMIM center dot Cl could easily be reused with no apparent loss in activity.

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External Sources

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  2. DOI: 10.1002/ejoc.201000188
  3. View record in Web of Science®
  4. WOS: 000279746300002

Library Notes

  1. Fiscal Year: FY2009-2010
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