Stereoselective synthesis of C-glycosides from carboxylic acids: the tandem Tebbe-Claisen approach.
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.
Godage
H Yasmin
HY
Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford, UK OX1 3QY.
Chambers
David J
DJ
Evans
Graham R
GR
Fairbanks
Antony J
AJ
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
D002264:Carboxylic Acids; D006027:Glycosides