Synthesis of carbohydrate derivatives using solid-phase work-up and scavenging techniques.
Methods to allow the clean preparation of oligosaccharides were investigated using techniques that do not require conventional column chromatography or an aqueous work-up. The route was designed to provide rapid access to oligosaccharides and is suitable for automation and parallel library formation. The research has focused on the glycosidations of a range of glycosyl acceptors with various selenophenyl glycosyl donors using iodine as an activator in the presence of DTBMP, a hindered organic base. Hydroxyl-containing contaminants were removed by scavenging with polymer-supported tosyl chloride.
MacCoss
Rachel N
RN
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
Brennan
Paul E
PE
Ley
Steven V
SV
D002240:Carbohydrate Sequence; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D007455:Iodine / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry
D006027:Glycosides; D009844:Oligosaccharides; D014105:Tosyl Compounds; D007455:Iodine