Synthesis of 2,3,4-Trideoxy-4,4-difluoro-d-ribo-hexopyranose Adenosines

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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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).