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【结 构 式】 
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【分子编号】35534 【品名】5-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-1,3-dioxan-2-one 【CA登记号】 |
【 分 子 式 】C11H12ClN5O3 【 分 子 量 】297.70088 【元素组成】C 44.38% H 4.06% Cl 11.91% N 23.52% O 16.12% |
合成路线1
该中间体在本合成路线中的序号：(VI)Treatment of diol (I) with 1,1'-carbonyldiimidazole produced the cyclic carbonate (II). Cleavage of the O-benzyl group of (II) by hydrogenolysis over Pd/C, gave alcohol (III), which was converted to mesylate (IV) by means of MsCl and Et3N. Subsequent coupling of (IV) with 2-amino-6-chloropurine (V) produced the 9-alkylated derivative (VI). The chlorine atom of (VI) was then removed by hydrogenolysis in the presence of Pd/C and Et3N to furnish (VII). Finally, opening of the cyclic carbonate group of (VII) with isopropanol upon heating in the presence of silica gel yielded the target compound.
| 【1】 Kim, D.-K.; Lee, N.; Kim, Y.-W.; Chang, K.; Kim, J.S.; Im, G.J.; Choi, W.S.; Jung, I.; Kim, T.S.; Hwang, Y.Y.; Min, D.S.; Um, K.A.; Cho, Y.B.; Kim, K.H.; Synthesis and evaluation of 2-amino-9-(3-hydroxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir. J Med Chem 1998, 41, 18, 3435. |
| 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) | 35523 | 2-[2-(benzyloxy)ethyl]-1,3-propanediol | C12H18O3 | 详情 | 详情 | |
| (II) | 35524 | 5-[2-(benzyloxy)ethyl]-1,3-dioxan-2-one | C13H16O4 | 详情 | 详情 | |
| (III) | 35525 | 5-(2-hydroxyethyl)-1,3-dioxan-2-one | C6H10O4 | 详情 | 详情 | |
| (IV) | 35526 | 2-(2-oxo-1,3-dioxan-5-yl)ethyl methanesulfonate | C7H12O6S | 详情 | 详情 | |
| (V) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (VI) | 35534 | 5-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-1,3-dioxan-2-one | C11H12ClN5O3 | 详情 | 详情 | |
| (VII) | 35527 | 5-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-dioxan-2-one | C11H13N5O3 | 详情 | 详情 |