title: Stereoselective synthesis of C-glycosides from carboxylic acids: the tandem Tebbe-Claisen approach.
abstract: A variety of beta- or alpha-C-glycosides may be readily accessed in an entirely stereoselective fashion from esters derived from the reaction of carboxylic acids and 3-hydroxy glycals, by way of a tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. Though of wide scope, for example allowing the synthesis of 1-6 linked C-disaccharides, the methodology does not currently allow the synthesis of C-glycosyl alpha-amino acids.
authors.affiliation: Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford, UK OX1 3QY.
authors.forename: H Yasmin
authors.initials: HY
authors.lastname: Godage
authors.forename: David J
authors.initials: DJ
authors.lastname: Chambers
authors.forename: Graham R
authors.initials: GR
authors.lastname: Evans
authors.forename: Antony J
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D006027:Glycosides