Synthesis of 5-dialkylaminomethyl-3′-azido and 3′-fluoro-2′,3′-dideoxyuridines for evaluation as anti-HIV agents
Research output: Contribution to journal › Journal article › Research › peer-review
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.
Original language | English |
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Journal | Monatshefte für Chemie Chemical Monthly |
Volume | 124 |
Issue number | 1 |
Pages (from-to) | 55-64 |
Number of pages | 10 |
ISSN | 0026-9247 |
DOIs | |
Publication status | Published - 1993 |
Externally published | Yes |
- AZT analogues, Herpes simplex virus, Human immunodeficiency virus, Nucleosides, convergent synthesis of, Uridines, 3′-azido-2′,3′-dideoxy, Uridines, 3′-fluoro-2′,3′-dideoxy
Research areas
ID: 249247215