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Synthesis 2001(6): 0929-0933
DOI: 10.1055/s-2001-13419
DOI: 10.1055/s-2001-13419
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 3′-Deoxy-3′-difluoromethyluridine and 2′-Deoxy-2′-difluoromethyluridine
Further Information
Received
12 December 2000
Publication Date:
15 October 2004 (online)
Publication History
Publication Date:
15 October 2004 (online)
Abstract
The synthesis of 3’-deoxy-3’-difluoromethyluridine (9) and 2’-deoxy-2’-difluoromethyluridine (7β) by hydrogenation of the corresponding difluoromethylene derivatives is described. A second synthesis of the latter has been performed. Starting from thymidine, a two-step procedure affords the benzylated furanoid glycal 12. Addition of dibromodifluoromethane gives the α-2’-deoxy-2’-bromodifluoromethylarabinose (13). This compound allowed an access to α- or β -2’-deoxy-2’-difluoromethyluridine via a SN2 type reaction on a α-halodeoxyarabinose species.
Keywords
addition reactions - fluorine - nucleosides - carbohydrates
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