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【结 构 式】 
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【药物名称】SK-1899 【化学名称】Acetic acid 4-(2-amino-9H-purin-9-yl)-2-(isopropoxycarbonyloxymethyl)butyl ester 【CA登记号】247081-81-8 【 分 子 式 】C16H23N5O5 【 分 子 量 】365.39221 |
【开发单位】SK Chemicals (Originator) 【药理作用】Anti-Hepatitis B Virus Drugs, Anti-Hepatitis Virus Drugs, Anti-Herpes Simplex Virus Drugs, Anti-Herpes Virus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs, Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems |
合成路线1
6-Deoxypenciclovir (I) was reacted with trimethyl orthoacetate in the presence of p-toluenesulfonic acid to give the cyclic orthoacetate intermediate (II) which, after aqueous quenching, afforded monoacetate ester (III). Subsequent treatment of (III) with isopropyl p-nitrophenyl carbonate (IV) using a catalytic amount of dimethylaminopyridine provided the target carbonate ester.
| 【1】 Kim, D.-K.; et al.; Synthesis and evaluation of 2-amino-9-(3-acyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines and 2-amino-9-(3-alkoxycarbonyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir. Bioorg Med Chem 1999, 7, 8, 1715. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 11643 | 2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol | C10H15N5O2 | 详情 | 详情 | |
| (II) | 35792 | 9-[2-(2-methoxy-2-methyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-ylamine; 9-[2-(2-methoxy-2-methyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine | C13H19N5O3 | 详情 | 详情 | |
| (III) | 35793 | 4-(2-amino-9H-purin-9-yl)-2-(hydroxymethyl)butyl acetate | C12H17N5O3 | 详情 | 详情 | |
| (IV) | 35794 | isopropyl 4-nitrophenyl carbonate | C10H11NO5 | 详情 | 详情 |