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-α-D-galactose. 1-Butyl-4-methylimidazolium chloride (BMIM·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 β-anomers, and the molten salt BMIM·Cl could easily be reused with no apparent loss in activity.
Original language | English (US) |
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Pages (from-to) | 3377-3381 |
Number of pages | 5 |
Journal | European Journal of Organic Chemistry |
Issue number | 18 |
DOIs | |
State | Published - Jun 2010 |
Externally published | Yes |
Keywords
- Carbohydrates
- Ionic liquids
- Koenigs-Knorr reaction
- Molten salts
- O-Glycosidation
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry