Synthesis of 2′, 3′-dideoxy-3′, 3′-difluoro and 2′, 3′-dideoxy-2′, 2′-difluoro-pyranosyl nucleosides analogues of gemcitabine
R Fernández, S Castillón
Index: Fernandez, Raul; Castillon, Sergio Tetrahedron, 1999 , vol. 55, # 28 p. 8497 - 8508
Full Text: HTML
Citation Number: 23
Abstract
The gem-difluoronucleosides 1 and 2, pyranosyl analogues of gemcitabine, have been synthesized from d-mannose and d-glucose respectively. The key steps were the formation of the difluoromethylene group by reaction of the corresponding ulose with DAST, and the glycosylation.
Related Articles:
Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides
[Toti, Kiran S.; Derudas, Marco; McGuigan, Christopher; Balzarini, Jan; Van Calenbergh, Serge European Journal of Medicinal Chemistry, 2011 , vol. 46, # 9 p. 3704 - 3713]
[Young, Robert J.; Shaw-Ponter, Sue; Hardy, George W.; Mills, Gail Tetrahedron Letters, 1994 , vol. 35, # 46 p. 8687 - 8690]