Trichloro-oxazolines as activated donors for aminosugar coupling.
Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions. [reaction: see text]
Donohoe
Timothy J
TJ
Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. timothy.donahoe@chem.ox.ac.uk
Logan
James G
JG
Laffan
David D P
DD
D000606:Amino Sugars / Q000737:chemistry*; D002240:Carbohydrate Sequence; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010080:Oxazoles / Q000737:chemistry*
D000606:Amino Sugars; D007202:Indicators and Reagents; D010080:Oxazoles