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Trichloro-oxazolines as activated donors for aminosugar coupling
Timothy J Donohoe1, James G Logan, David D P Laffan
1Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. timothy.donahoe@chem.ox.ac.uk
Organic Letters
|December 20, 2003
Abstract:
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]