Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents
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Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylamino-methyluracils 11a-f in 65-85% yield. Compounds 11a-f were silylated with hexamethyldisilazane and coupled with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside 4 and 3-azido-2,3-dideoxy-D-erythro-pentofuranoside 7 to give the corresponding 3′-fluoro-2′,3′-dideoxynucleosides 13a-f and 3′-azido-2′,3′-dideoxy nucleosides 16d, f, respectively, by using trimethylsilyl trifluoromethanesulfonate as a catalyst. Deprotection of the 5-O-(4-phenylbenzoyl) protected nucleosides 13a-f and 16d, f with saturated methanolic ammonia and separation by chromatography yielded the new derivatives of 2′,3′-dideoxy-3′-fluorouridines 14a-f and 15a-f and 2′,3′-dideoxy-3′-azidouridines 17d, f and 18d, f.
Originalsprog | Engelsk |
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Tidsskrift | Monatshefte für Chemie Chemical Monthly |
Vol/bind | 124 |
Udgave nummer | 1 |
Sider (fra-til) | 55-64 |
Antal sider | 10 |
ISSN | 0026-9247 |
DOI | |
Status | Udgivet - 1993 |
Eksternt udgivet | Ja |
Bibliografisk note
(Ekstern)
ID: 249247215