Stereoselective entry to beta-linked C-disaccharides using a carbon-Ferrier reaction.
[structure: see text] The synthesis of unsaturated beta-linked C-disaccharides by the Lewis acid-mediated reaction of 3-O-acetylated glycals with monosaccharide-derived alkenes is described. Deprotection and selective hydrogenation of an exocyclic carbon-carbon double, in the presence of an endocyclic double bond, for representative targets is also illustrated.
Gemmell
Natasha
N
School of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AD, UK.
Meo
Paul
P
Osborn
Helen M I
HM
D000107:Acetylation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D013237:Stereoisomerism
D004187:Disaccharides; D007202:Indicators and Reagents