|
【结 构 式】 
|
【药物名称】 【化学名称】1-[4-(Allyloxycarbonylamino)-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl]-1-deoxy-beta-D-ribofuranuronic acid 【CA登记号】396684-66-5 【 分 子 式 】C13H14FN3O8 【 分 子 量 】359.27023 |
【开发单位】Kolon Industries (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
The silylated 5-fluorocytosine (I) is coupled with D-ribofuranose tetraacetate (II) in the presence of SnCl4 in acetonitrile to afford the triacetyl 5-fluorocytidine (III). Acylation of (III) with allyl chloroformate (IV) yields carbamate (V). Then, methanolysis of the acetate ester groups of (V) provides 5-fluoro-N-(allyloxycarbonyl)cytidine (VI). Finally, selective oxidation of the primary alcohol group of (VI) with oxygen and PtO2 gives the target carboxylic acid
| 【1】 Kim, K.-H.; Kim, J.-Y; Lee, K-H; Noh, M.-J.; Kim, Y.-C.; Park, H.-J.; Synthesis and biological activity of the new 5-fluorocytosine derivatives, 5'-deoxy-N-alkyloxycarbonyl-5-fluorocytosine-5'-carboxylic acid. Bioorg Med Chem Lett 2002, 12, 3, 483. |
| 【2】 Lee, K.-H.; Kim, J.-Y.; Kim, Y.-C.; Kim, K.-H.; Park, H.-J.; Noh, M.-J.; Park, Y.-S.; Cho, S.-M. (Kolon Industries, Inc.); 5'-Deoxy-N-(substd. oxycarbonyl)-5-fluorocytosine and derivs. thereof, method of preparing same, and anticancer compsn. comprising same as active ingredients. WO 0211668 . |
| 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) | 36959 | 5-fluoro-N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine; N-[5-fluoro-2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-N-(trimethylsilyl)amine | C10H20FN3OSi2 | 详情 | 详情 | |
| (II) | 33835 | (2R,3R,4R,5S)-4,5-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-3-furanyl acetate | 13035-61-5 | C13H18O9 | 详情 | 详情 |
| (III) | 60387 | (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]tetrahydro-3-furanyl acetate | C15H18FN3O8 | 详情 | 详情 | |
| (IV) | 38115 | 3-[(chlorocarbonyl)oxy]-1-propene | 2937-50-0 | C4H5ClO2 | 详情 | 详情 |
| (V) | 60388 | (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[4-{[(allyloxy)carbonyl]amino}-5-fluoro-2-oxo-1(2H)-pyrimidinyl]tetrahydro-3-furanyl acetate | C19H22FN3O10 | 详情 | 详情 | |
| (VI) | 60389 | allyl 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-fluoro-2-oxo-1,2-dihydro-4-pyrimidinylcarbamate | C13H16FN3O7 | 详情 | 详情 |
Extended Information