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【结 构 式】 
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【分子编号】57567 【品名】4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid 【CA登记号】 |
【 分 子 式 】C34H33IN2O10 【 分 子 量 】756.54797 【元素组成】C 53.98% H 4.4% I 16.77% N 3.7% O 21.15% |
合成路线1
该中间体在本合成路线中的序号：(IV)5-Iodo-2'-deoxyuridine (I) is protected at the primary hydroxyl group with 4,4'-dimethoxytrityl chloride to afford the 5'-O-trityl derivative (II). Subsequent esterification of the remaining hydroxyl group of (II) with succinic anhydride (III) yields the succinate mono-ester (IV). Acid (IV) is then coupled with diethylene glycol in the presence of DCC to produce (V). The O-trityl group of (V) is finally removed by treatment with formic acid, to give the title compound.
| 【1】 Bonina, F.P.; et al.; New oligoethylene ester derivatives of 5-iodo-2'-deoxyuridine as dermal prodrugs: Synthesis, physicochemical properties, and skin permeation studies. J Pharm Sci 2002, 91, 1, 171. |
| 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) | 31154 | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione | 54-42-2 | C9H11IN2O5 | 详情 | 详情 |
| (II) | 57566 | 1-((2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydro-2-furanyl)-5-iodo-2,4(1H,3H)-pyrimidinedione | C30H29IN2O7 | 详情 | 详情 | |
| (III) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |
| (IV) | 57567 | 4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid | C34H33IN2O10 | 详情 | 详情 | |
| (V) | 57568 | 1-{(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl} 4-[2-(2-hydroxyethoxy)ethyl] succinate | C38H41IN2O12 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)5-Iodo-2'-deoxyuridine (I) is protected at the primary hydroxyl group with 4,4'-dimethoxytrityl chloride to afford the 5'-O-trityl derivative (II). Subsequent esterification of the remaining hydroxyl group of (II) with succinic anhydride (III) yields the succinate mono-ester (IV). Acid (IV) is then coupled with triethylene glycol in the presence of DCC to produce (V). The O-trityl group of (V) is finally removed by treatment with formic acid, to give the title compound.
| 【1】 Bonina, F.P.; et al.; New oligoethylene ester derivatives of 5-iodo-2'-deoxyuridine as dermal prodrugs: Synthesis, physicochemical properties, and skin permeation studies. J Pharm Sci 2002, 91, 1, 171. |
| 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) | 31154 | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione | 54-42-2 | C9H11IN2O5 | 详情 | 详情 |
| (II) | 57566 | 1-((2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydro-2-furanyl)-5-iodo-2,4(1H,3H)-pyrimidinedione | C30H29IN2O7 | 详情 | 详情 | |
| (III) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |
| (IV) | 57567 | 4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid | C34H33IN2O10 | 详情 | 详情 | |
| (V) | 57569 | 1-{(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl} 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl} succinate | C40H45IN2O13 | 详情 | 详情 |