476209-84-4Relevant academic research and scientific papers
A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone
Choudhury, Anusuya,Jin, Fuqiang,Wang, Dengjin,Wang, Zhe,Xu, Guoyou,Nguyen, Dieu,Castoro, John,Pierce, Michael E.,Confalone, Pat N.
, p. 247 - 250 (2007/10/03)
Anti-HIV agent β-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly syn-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation.
2'-Fluoro-4'-thio-2',3'-unsaturated nucleosides: anti-HIV activity, resistance profile, and molecular modeling studies.
Chong, Youhoon,Choo, Hyunah,Schinazi, Raymond F,Chu, Chung K
, p. 611 - 615 (2007/10/03)
Both D- and L-2'-fluoro-4'-thio-2',3'-unsaturated nucleosides were synthesized and their anti-HIV activity against the drug sensitive virus and lamivudine-resistant mutant (M184V) were evaluated. In vitro antiviral evaluation indicated that the L-isomers
Stereoselective synthesis and antiviral activity of d-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4 ′-thionucleosides
Chong, Youhoon,Choo, Hyunah,Choi, Yongseok,Mathew, Judy,Schinazi, Raymond F.,Chu, Chung K.
, p. 4888 - 4898 (2007/10/03)
As 2′,3′-didehydro-2′,3′-dideoxy-2′ -fluoronucleosides have exhibited interesting antiviral effects against HIV-1 as well as HBV, it is of interest to synthesize the isosterically substituted 4′-thionucleosides in which 4′-oxygen is replaced by a sulfur a
