Base-catalyzed degradation of permethylated 3-O-glycosyl- glycopyranosid-2-uloses.
In a modification of the Svensson degradation, otherwise permethylated glycopyranosid-2-uloses bearing 4-O-glycosyl substituents are formed by the Swern oxidation. Base-catalyzed elimination on treatment with triethylamine then gives 4-deoxy-3-O-methylglyc-3-enopyranosid-2-ulose-terminat ed oligosaccharides with liberation of glycosyl substituents as reducing sugars but without further degradation. Mild acid hydrolysis results in removal of the unsaturated sugar residues so that the overall depolymerization occurs with net loss only of the initially oxidized sugar residue.
Aspinall
G O
GO
Department of Chemistry, York University, Toronto, Ontario, Canada.
Capek
P
P
Carpenter
R C
RC
Szafranek
J
J
D002240:Carbohydrate Sequence; D008745:Methylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D011134:Polysaccharides / Q000737:chemistry
D009844:Oligosaccharides; D011134:Polysaccharides