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Synthesis of 5-homologous AZT and D4T derivatives
U Kjaersgaard1, E B Pedersen, C Nielsen
1Department of Chemistry, Odense University, Denmark.
Acta Chemica Scandinavica (Copenhagen, Denmark : 1989)
|October 1, 1992
Abstract:
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.