Synthesis of 1-(3-alkyl-2,3-dideoxy-D-pentofuranosyl)uracils with potential anti-HIV activity.
1-(3-Alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)uracils and 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-threo-pentofuranosyl)uracils have been prepared from (E)-4,5-di-O-acetyl-2,3-dideoxy-aldehydo-D-glycero-pent-2-enose by a Michael addition reaction of the appropriate organocopper reagent followed in subsequent order by glycosidation of the resulting 3-alkyl-4,5-diacetoxypentanal with methanolic hydrogen chloride, protection with p-methoxybenzoyl chloride, and trimethylsilyl triflate catalyzed coupling with 2,4-di-O-(trimethylsilyl)uracil. The nucleosides were deprotected by treatment with 33% methylamine in absolute ethanol and separated by reversed-phase HPLC.
Walczak
K
K
Department of Chemistry, Odense University, Denmark.
Pedersen
E B
EB
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D006678:HIV / Q000187:drug effects; D006851:Hydrochloric Acid; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D015394:Molecular Structure; D014529:Uridine / Q000031:analogs & derivatives*; D014994:Xylose
D000998:Antiviral Agents; D015224:Dideoxynucleosides; D003300:Copper; D014994:Xylose; D006851:Hydrochloric Acid; D014529:Uridine; D000432:Methanol