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Journal article

Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Abstract:
Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a newapproachto the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1, 4-dideoxy-1,4-imino-D-mannitol) was the acetonation of D-mannose.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c6ob00531d

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Funding agency for:
Fleet, G
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Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Organic and Biomolecular Chemistry Journal website
Volume:
14
Issue:
19
Pages:
4488-4498
Publication date:
2016-04-01
Acceptance date:
2016-04-14
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Source identifiers:
626333
Pubs id:
pubs:626333
UUID:
uuid:08759600-fc77-4503-9308-b5a5c20042e5
Local pid:
pubs:626333
Deposit date:
2016-07-04

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