New synthesis of 2',3'-didehydro-2',3'-dideoxynucleosides.
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.
Abdel-Megied
A E
AE
Department of Chemistry, Odense University, Denmark.
Hansen
P
P
Pedersen
E B
EB
Nielsen
C M
CM
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
D000998:Antiviral Agents; D015224:Dideoxynucleosides; D018119:Stavudine