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  • Title: Trichloro-oxazolines as activated donors for aminosugar coupling.
    Author: Donohoe TJ, Logan JG, Laffan DD.
    Journal: Org Lett; 2003 Dec 25; 5(26):4995-8. PubMed ID: 14682748.
    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]
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