超大的飞机:喷昔洛韦 [CAS:39809-25-1]合成路线图解??有机化学网
来源:百度文库 编辑:九乡新闻网 时间:2024/07/14 13:30:54
药物详细合成路线
Chemical Name: 9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine Generic Name: 喷昔洛韦;Penciclovir Other Names: Penciclovir;BRL-39123;Denavir;Vectavir CAS: 39809-25-1 Related CAS: 97845-62-0 (Na salt) Formula: C10H15N5O3 Mole Weight: 253.26275 structure:![](http://image28.360doc.cn/DownloadImg/2011/05/0406/11436023_1.gif)
![](http://image28.360doc.cn/DownloadImg/2011/05/0406/11436023_2.gif)
Route 2 This compound has been obtained by two similar ways:1) The reaction of 6-chloropurine-2-amine (I) with 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (II) by means of K2CO3 in DMF gives the expected condensation product (III), which is methanolized with HCl/methanol yielding 2-[2-(2-amino-6-methoxypurin-9-yl)ethyl]malonic acid dimethyl ester (IV). The reduction of (IV) with NaBH4 in tert-butanol/methanol affords the corresponding diol (V), which is finally converted into pecnciclovir by hydrolysis with 2N NaOH.2) The reaction of purine (I) with 3-bromopropane-1,1,1-tricarboxylic acid triethyl ester (VI) by means ofK2CO3 in DMF gives the expected condensation product (VII), which is partially decarboxylated with sodium methoxide in methanol yielding 2-[2-(2-amino-6-chloropurin-9-yl)ethyl]malonic acid diethyl ester (VIII). The reduction of (VIII) with NaBH4 in tert-butanol/methanol followed by acetylation with acetic anhydride affords the corresponding diol diacetate (IX), which is finally converted into penciclovir by hydrlysis with 2N HCl.
![](http://image28.360doc.cn/DownloadImg/2011/05/0406/11436023_3.gif)
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