SYNTHESIS OF 5-DIALKYLAMINOMETHYL-3'-AZIDO AND 3'-FLUORO-2',3'-DIDEOXYURIDINES FOR EVALUATION AS ANTI-HIV AGENTS

Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 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 t...

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Bibliographic Details
Published inMonatshefte für Chemie Vol. 124; no. 1; pp. 55 - 64
Main Authors MOTAWIA, MS, JORGENSEN, PT, LARNKJAER, A, PEDERSEN, EB, NIELSEN, C
Format Journal Article
LanguageEnglish
Published VIENNA Springer Nature 01.01.1993
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Summary:Uracil (8) was substituted in a Mannich reaction to give the 5-substituted dialkylaminomethyluracils 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.
ISSN:0026-9247
DOI:10.1007/BF00808509