Synthesis of Novel Fluoro Carbocyclic Purine Nucleoside Analogues

Synthesis and applications of fluorinated nucleoside analogues

“…The carbocyclic 2 0 ,3 0 -dideoxy-2 0 -fluoro-3 0 -C-hydroxymethylpurine nucleosides 61 and 63, designed as potential inhibitors of HIV and HSV, have been synthesized by Samuelsson and coworkers [28,30]. Their synthesis started from the cyclopentanone derivative 57, which was treated with TMSOTf/Et 3 N followed by Selectfluor to give the fluoroketones 58 (Scheme 12).…”

Recent advances in the synthesis of fluorinated nucleosides

“…In addition, the L-isomers 120 were also synthesized by Jeong's group using a similar route. 102,103 Recently, Damha's group have described an improved synthesis of 2 0 -deoxy-2 0 b-fluoro-5-methyl-4-thio-arabino-uridine (4 0 S-FMAU, 119, B¼T) and further pursued the conformational analysis of 4 0 S-FMAU using coupling constants and the PSEUROT program. 104 tional analysis of 4 0 S-FMAU showed that the replacement of oxygen by the cognate sulfur atom at the 4 0 -position led to a decrease in the magnitude of the C5 0 -base steric effects, various gauche effects and a corresponding shift to a North conformation.…”

“…118,119 Their synthesis started from the cyclopentanone derivative 154, which was treated with TMSOTf/Et 3 N followed by F-TEDA-BF 4 to deliver the fluoroketones 155 (Scheme 27). Stereoselective reduction of the ketones 155 with LS-Selectride gave two alcohols 156 and 157, which were separated by column chromatography.…”

Effect of terminal 3′-hydroxymethyl modification of an RNA primer on nonenzymatic primer extension

“…1). Several previous reports have described the synthesis of nucleotide analogs with an extended sugar phosphate backbone, typically beginning with a modified abasic sugar or carbocycle [20][21][22][23][24][25] followed by glycosylation to incorporate the purine or pyrimidine nucleobase. This approach leads to the formation of unwanted regioisomers that are difficult to separate.…”