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New synthesis of 2',3'-didehydro-2',3'-dideoxynucleosides
A E Abdel-Megied1, P Hansen, E B Pedersen
1Department of Chemistry, Odense University, Denmark.
Acta Chemica Scandinavica (Copenhagen, Denmark : 1989)
|November 1, 1991
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.