Synthesis of 5-homologous AZT and D4T derivatives.
The 3'-iodonucleosides 4 have been synthesized by condensation of silylated 5-alkyluracils 2 with methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofur  anoside (3). 4 was treated with sodium azide and the deprotected nucleoside 5 was subsequently obtained by treatment with tetrabutylammonium fluoride. The nucleoside 4 produced the corresponding 2',3'-didehydro-2',3'-dideoxy nucleoside 6 and 3',4'-didehydro-2',3'-dideoxy nucleoside 7 in elimination reactions on treatment with sodium methoxide.
Kjaersgaard
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U
Department of Chemistry, Odense University, Denmark.
Pedersen
E B
EB
Nielsen
C
C
el-Torgoman
A M
AM
D000998:Antiviral Agents / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D018119:Stavudine; D015215:Zidovudine / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D000998:Antiviral Agents; D015224:Dideoxynucleosides; D015215:Zidovudine; D018119:Stavudine