title: Cyclopropenium cation promoted dehydrative glycosylations using 2-deoxy- and 2,6-dideoxy-sugar donors.
abstract: Dehydrative glycosylation reactions using 2-deoxy- and 2,6-dideoxy-sugar donors promoted by a combination of 3,3-dichloro-1,2-diphenylcyclopropene and tetrabutylammonium iodide (TBAI) are described. The reactions are α-selective and proceed under mild conditions at room temperature without the need for special dehydrating agents. The reaction is shown to be effective with a number of glycosyl acceptors, including those possessing acid and base sensitive functionality.
authors.affiliation: Department of Chemistry, Tufts University, Medford, Massachusetts 02155, United States.
authors.forename: Jason M
authors.initials: JM
authors.lastname: Nogueira
authors.forename: Son Hong
authors.initials: SH
authors.lastname: Nguyen
authors.forename: Clay S
authors.initials: CS
authors.lastname: Bennett
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D003521:Cyclopropanes; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium