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Synthesis 2009(4): 602-608
DOI: 10.1055/s-0028-1083331
DOI: 10.1055/s-0028-1083331
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2,3,4-Trideoxy-4,4-difluoro-d-ribo-hexopyranose Adenosines
Further Information
Received
3 September 2008
Publication Date:
27 January 2009 (online)
Publication History
Publication Date:
27 January 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200904/lookinside/thumbnails/10.1055-s-0028-1083331-1.jpg)
Abstract
A novel synthetic route to 2,3,4-trideoxy-4,4-difluoro-β-d-ribo-hexopyranose adenosine and 2,3,4-trideoxy-2,3-didehydro-4,4-difluoro-β-d-ribo-hexopyranose adenosine has been developed. The approach highlights the highly regio- and stereoselective palladium-catalyzed glycosylation of Boc-protected pyranose, which was prepared from the oxidation-cyclization of a difluorinated diol. The diol was provided through ozonization and Lindlar reduction of optically pure enynic alcohol.
Key words
nucleosides - fluorinated compounds - palladium-catalyzed glycosylation
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References
Further details of the crystal structure investigation can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK (CCDC deposition No. 694847).