Synthesis of 3 '-deoxy-3 '-difluoromethyluridine and 2 '-deoxy-2 '-difluoromethyluridine

Authors
Marcotte, S Gerard, B Pannecoucke, X Feasson, C Quirion, JC
Citation
S. Marcotte et al., Synthesis of 3 '-deoxy-3 '-difluoromethyluridine and 2 '-deoxy-2 '-difluoromethyluridine, SYNTHESIS-S, (6), 2001, pp. 929-933
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
6
Year of publication
2001
Pages
929 - 933
Database
ISI
SICI code
0039-7881(200105):6<929:SO3''A>2.0.ZU;2-K
Abstract
The synthesis of 3'-deoxy-3'-difluoromethyluridine (9) and 2'-deoxy-2'-difl uoromethyluridine (7 beta) by hydrogenation of the corresponding difluorome thylene derivatives is described. A second synthesis of the latter has been pet-formed. Starting from thymidine, a two-step procedure affords the benz ylated furanoid glycal 12. Addition of dibromodifluoromethane gives the alp ha -2'-deoxy-2'-bromodifluoromethylarabinose (13). This compound allowed an access to alpha- or beta -2'-deoxy-2'-difluoromethyluridine via a S(N)2 ty pe reaction on a alpha -halodeoxyarabinose species.