Synthesis of 2′,3′-Dideoxy-2′-difluoromethyl Azanucleosides

Xiao-Long Qiu; Feng-Ling Qing

doi:10.1055/s-2004-815932

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Synthesis 2004(3): 334-340
DOI: 10.1055/s-2004-815932

PAPER

Synthesis of 2′,3′ - Dideoxy-2′-difluoromethyl Azanucleosides

Xiao-Long Qiu^a, 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. China
^b College of Chemistry and Chemical Engineering, Donghua University, 1882 West Yanan Lu, Shanghai 200051, P. R. China
Fax: +86(21)64166128; e-Mail: flq@mail.sioc.ac.cn;

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Publication History

Received 30 October 2003
Publication Date:
26 January 2004 (online)

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Abstract

Methyl (2S,4S)-N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate (9a) was synthesized from trans-4-hydroxy-l-proline (5). Compound 9a was converted to (5S,3S)-N-benzyloxycarbonyl-5-(tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-pyrrolidone (15) over 4 steps in 66% yield, which was used as a key intermediate for the synthesis of 2′,3′-dideoxy-2′-difluoromethyl azanucleosides

Key words

fluorine-containing nucleoside - azanucleoside - pyroglutamate - difluoromethylenation - glycosylation reaction

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