Glycosylation with Trichloroacetimidates in Ionic Liquids: Influence of the Reaction Medium on the Stereochemical Outcome
- 16 August 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (19) , 7765-7768
- https://doi.org/10.1021/jo050704x
Abstract
The glycosylation with trichloroacetimidates derived from different glycopyranoses bearing a nonparticipating group at C-2 was explored in different ionic liquids as solvents. The stereoselectivity of the reaction was significantly affected by the reaction media and by the anomeric configuration of the donor.Keywords
This publication has 11 references indexed in Scilit:
- Ionic liquids: solvent properties and organic reactivityJournal of Physical Organic Chemistry, 2004
- Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosidesTetrahedron, 2004
- Catalytic and Stereoselective Glycosylation with Glucosyl ThioformimidatesBulletin of the Chemical Society of Japan, 2003
- Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquidAnalytical and Bioanalytical Chemistry, 2003
- Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groupsTetrahedron: Asymmetry, 2001
- The Room Temperature Ionic Liquid 1‐Ethyl‐3‐methylimidazolium Tetrafluoroborate: Electrochemical Couples and Physical PropertiesJournal of the Electrochemical Society, 1997
- Hydrophobic, Highly Conductive Ambient-Temperature Molten SaltsInorganic Chemistry, 1996
- Anomeric-Oxygen Activation for Glycoside Synthesis: The Trichloroacetimidate MethodAdvances in Carbohydrate Chemistry and Biochemistry, 1994
- Recent progress in O-glycosylation methods and its application to natural products synthesisChemical Reviews, 1993
- Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activityJournal of Medicinal Chemistry, 1986