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Synthesis 2009(4): 602-608  
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

Jun Xua, Xingang Zhanga, Xiao-Long Qiua, Feng-Ling Qing*a,b
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
b College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, P. R. of China
Fax: +(86)2164166128; e-Mail: flq@mail.sioc.ac.cn;
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Publication History

Received 3 September 2008
Publication Date:
27 January 2009 (online)

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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).