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

被引：4
作者：
MOTAWIA, MS
JORGENSEN, PT
LARNKJAER, A
PEDERSEN, EB
NIELSEN, C
机构：
[1] ODENSE UNIV,DEPT CHEM,CAMPUSVEJ 55,DK-5230 ODENSE,DENMARK
[2] STATENS SERUMINST,DEPT VIROL,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK
来源：
MONATSHEFTE FUR CHEMIE | 1993年 / 124卷 / 01期
关键词：
NUCLEOSIDES; CONVERGENT SYNTHESIS OF; URIDINES; 3'-AZIDO-2'; 3'-DIDEOXY; 3'-FLUORO-2'; AZT ANALOGS; HUMAN IMMUNODEFICIENCY VIRUS; HERPES SIMPLEX VIRUS;
D O I：
10.1007/BF00808509
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
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页码：55 / 64
页数：10
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