Synthesis of all configurational isomers of 1,6-anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-d-hexopyranoses
Language English Country United States Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
20397714
DOI
10.1021/jo1000912
Knihovny.cz E-resources
- MeSH
- Azides chemistry MeSH
- Molecular Structure MeSH
- Carbohydrates chemical synthesis chemistry MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Azides MeSH
- Carbohydrates MeSH
We have prepared a full series of 1,6-anhydro-2,3,4-trideoxy-4-fluoro-2,3-epimino-beta-d-hexopyranoses. The key step was the reaction of azido sulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH(4) reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of d-mannoepimine from a readily available 3-benzylamino derivative was also developed.
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