title: New synthesis of 2',3'-didehydro-2',3'-dideoxynucleosides.
abstract: The 3'-iodonucleoside 4 and the 3'-O-methylsulfonylthymidine 9 have been synthesized by condensation of silylated uracils 2 with methyl 5-O-tert-butyldiphensilyl-2,3-dideoxy-3-iodo-D-threo-pentofuran oside (3) and methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-methylsulfonyl-D-erythro- pentofuranoside (8), respectively. The nucleoside 4 and 9 produced the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 5 in an elimination reaction on treatment with sodium methoxide. The compounds 5b showed no antiviral activity against HIV-1.
authors.affiliation: Department of Chemistry, Odense University, Denmark.
authors.forename: A E
authors.initials: AE
authors.lastname: Abdel-Megied
authors.forename: P
authors.initials: P
authors.lastname: Hansen
authors.forename: E B
authors.initials: EB
authors.lastname: Pedersen
authors.forename: C M
authors.initials: CM
authors.lastname: Nielsen
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D018119:Stavudine
chemical_list: D000998:Antiviral Agents; D015224:Dideoxynucleosides; D018119:Stavudine