A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity |
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Authors: | Kaname Sasaki |
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Affiliation: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan |
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Abstract: | The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation was significantly affected by the ionic liquid solvent. 1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate (C6mim[OTf]), containing a trifluoromethanesulfonate anion, and 1-(3-cyanopropyl)-3-methylimidazolium trifluoromethanesulfonimidide (CNC3mim[NTf2]), possessing a cyano group at the side chain of the imidazolium cation, gave the β-stereoselectivity. |
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Keywords: | Carbohydrate Glycosidation Glycosyl fluoride Ionic liquid Designability |
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