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Paper | Regular issue | Vol 36, No. 4, 1993, pp.681-690
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6135
5-Amino Derivatives of 2’,3’-Dedeoxynucleosides for Evaluation of Anti-HIV Activity

Ahmed E.-S. Abdel-Megied, Henrik Pedersen, Erik B. Pedersen,* and Claus Nielsen

*Department of Chemistry, Odense University, Campusvej 55 DK-5230 Odense M., Denmark


Reaction of protected 2,3-dideoxy-D-ribose (2) with silylatd 5-amino derivatives of uracil using trimethylsilyl trifluoromethanesulfonate as catalyst afforded the 2’,3’-dideoxynucleosides (3a-d) which were deprotected with methanolic ammonia and separated by chromatography to give α-anomers (4a-d) and β-anomers (5a-d). Compounds (3a-c) were converted to 4-(1,2,4-triazol-1-yl) derivatives (6a-c). Ammonia in dioxane converted the 4-(1,2,4-triazole-1-yl)pyrimidin-2(1H)-one moiety into cytosin-1-yl. In case of 6b, 4-methoxypyrimidin-2-one 2,3-dideoxyriboside was accomplised via transformation of the 4-triazolyl moiety with methanol on silica. Mathanolic ammonia was used for deprotection of the sugar moiety to afford 7-10.