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Trichloro-oxazolines as activated donors for aminosugar coupling.

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]
Publication status:
Published

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Publisher copy:
10.1021/ol0359620

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
5
Issue:
26
Pages:
4995-4998
Publication date:
2003-12-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:04ed5ac4-65a9-404c-b000-d46fe344a1cd
Source identifiers:
32580
Local pid:
pubs:32580

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