Synthesis of 3'-trifluoromethyl nucleosides as potential antiviral agents.
1,2-Di-O-acetyl-3-deoxy-3-trifluoromethyl-5-O-benzoyl-beta-D-ribofuranos e was synthesized from the precursor keto sugar by the use of Ruppert's reagent (CF3SiMe3) as the source of a nucleophilic trifluoromethyl group. Coupling of this trifluoromethyl sugar with nucleobases and elaboration gave novel deoxy and dideoxynucleosides. A single crystal X-ray analysis confirmed the structure and stereochemistry. The deoxynucleosides were converted through an elimination reaction to their dideoxydidehydro derivatives.
Sharma
P K
PK
Department of Chemistry, University of Iowa, Iowa City 52242, USA.
Nair
V
V
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002478:Cells, Cultured / Q000187:drug effects; D018360:Crystallography, X-Ray; D015497:HIV-1 / Q000187:drug effects / Q000502:physiology; D006801:Humans; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis*; D014779:Virus Replication / Q000187:drug effects
C417405:1,2-di-O-acetyl-3-deoxy-3-trifluoromethyl-5-O-benzoyl-ribofuranose; D000998:Antiviral Agents; D009705:Nucleosides