SYNTHESIS OF 1-(3-ALKYL-2,3-DIDEOXY-D-PENTOFURANOSYL)URACILS WITH POTENTIAL ANTI-HIV ACTIVITY

被引：0
|
作者：
WALCZAK, K
PEDERSEN, EB
机构：
[1] Department of Chemistry, Odense University, Odense M
来源：
ACTA CHEMICA SCANDINAVICA | 1991年 / 45卷 / 09期
关键词：
D O I：
10.3891/acta.chem.scand.45-0930
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
1-(3-Alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)uracils and 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-threo-pentofuranosyl)uracils have been prepared from (E)-4,5-di-O-acetyl-2,3-dideoxy-aldehydo-D-glycero-pent-2-enose by a Michael addition reaction of the appropriate organocopper reagent followed in subsequent order by glycosidation of the resulting 3-alkyl-4,5-diacetoxypentanal with methanolic hydrogen chloride, protection with p-methoxybenzoyl chloride, and trimethylsilyl triflate catalyzed coupling with 2,4-di-O-(trimethylsilyl)uracil. The nucleosides were deprotected by treatment with 33% methylamine in absolute ethanol and separated by reversed-phase HPLC.
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页码：930 / 934
页数：5
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