D-galacturonic acid derivatives as acceptors and donors in glycosylation reactions.
Jones oxidation of suitably protected allyl beta-D-galactopyranosides and subsequent esterification were reinvestigated. Partial deprotection of the resulting D-galacturonic acid derivatives afforded compounds suitable for transformation into glycosyl acceptors. The synthesis of 2-, 3-, and 4-trityl ethers, relying on efficient differential protecting-group strategies, is described. Trityl-cyanoethylidene condensation of these trityl ethers, leading to the protected disaccharide units beta-D-GalpA-(1-->2)-D-GalpA and beta-D-GalpA-(1-->3)-GalpA with high stereoselectivity, is demonstrated. A beta-D-GalpA-(1-->4)-D-GalpA disaccharide was also prepared.
Vogel
C
C
Universität Rostock, Fachbereich Chemie, Germany.
Steffan
W
W
Ott AYa
Betaneli
V I
VI
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D005697:Galactosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006603:Hexuronic Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data
D004187:Disaccharides; D005697:Galactosides; D006603:Hexuronic Acids; C007819:galacturonic acid