819799-79-6Relevant academic research and scientific papers
Synthesis and antiviral evaluation of 2′,2′,3′,3′-tetrafluoro nucleoside analogs
Sari, Ozkan,Bassit, Leda,Gavegnano, Christina,McBrayer, Tamara R.,McCormick, Louise,Cox, Bryan,Coats, Steven J.,Amblard, Franck,Schinazi, Raymond F.
, p. 642 - 644 (2017/01/25)
Herein, we report the synthesis of novel 2′,2′,3′,3′-tetrafluorinated nucleoside analogs along with their phosphoramidate prodrugs. A tetrafluoro ribose moiety was coupled with different Boc/benzoyl-protected nucleobases under Mitsunobu conditions. After deprotection, tetrafluorinated nucleosides 13b, 14b, 20b-22b were reacted with phenyl-(isopropoxy-L-alaninyl)-phosphorochloridate to afford corresponding monophosphate prodrugs 24b–28b. All synthesized compounds were evaluated against several DNA and RNA viruses including HIV, HBV, HCV, Ebola and Zika viruses.
Enantioselective synthesis of tetrafluorinated ribose and fructose
Linclau, Bruno,Boydell, A. James,Timofte, Roxana S.,Brown, Kylie J.,Vinader, Victoria,Weymouth-Wilson, Alexander C.
experimental part, p. 803 - 814 (2009/06/19)
A perfluoroalkylidene lithium mediated cyclisation approach for the enantioselective synthesis of a tetrafluorinated aldose (ribose) and of a tetrafluorinated ketose (fructose), both in the furanose and in the pyranose form, is described.
Enantioselective synthesis of tetrafluoroethylene-containing monosaccharides
Boydell, A. James,Vinader, Victoria,Linclau, Bruno
, p. 5677 - 5679 (2007/10/03)
A Sharpless asymmetric dihydroxylation of the commercially available building block 1 affords the common chiral intermediate 2 for the synthesis of the fluoridated monosaccharides 3-5 (Bn=benzyl).
