阿巴卡韦的合成  

Synthesis of Abacavir

作　　者：王峥[1] 施振华[1] 周伟澄[1] 

机构地区：[1]上海医药工业研究院,上海200437

出　　处：《中国医药工业杂志》2007年第1期1-4,共4页Chinese Journal of Pharmaceuticals

基　　金：科技部863计划项目(2004AA2Z3751)

摘　　要：环戊二烯和乙醛酸经Diels-Alder环合、丁酰化、酶水解得(1R,4S,5R)-(–)-4-endo-4-羟基-2-氧杂二环[3.3.0]辛-7-烯-3-酮,再经LiAlH4还原、NaIO4氧化、NaBH4还原、乙酰化得(1R,2R)-2-乙酰氧基环戊-3-烯-1-甲醇乙酸酯,再经与2-氨基-6-环丙胺基-9H-嘌呤缩合、NaOH水解后制得抗艾滋病药物阿巴卡韦,总收率约3%(以乙醛酸计)。Cyclopentadiene and glyoxylic acid underwent the Diels-Alder reaction, acylation with butyric anhydride, lipase enzymatic hydrolysis to get （1R,4S,SR）-（-）-4-endo-hydroxy-2-oxabicyclo [3.3.0] oct-7-en-3-one （4）, which was successively reduced with LiAIH4, oxidized with NaIO4, reduced with NaBH4 and acelated with acetic anhydride to give （1R,2R）-2-acetoxycyclopent-3-en-1-methanol acetate （9）. 9 was converted to an anti-HIV drug abacavir by condensation with 2-amino-6-cyclopropylamino-9H-purine and hydrolysis in sodium hydroxide solution.

关 键 词：阿巴卡韦 抗病毒药 艾滋病 合成 

分 类 号：R978.7[医药卫生—药品]