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【结 构 式】 
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【分子编号】41894 【品名】 【CA登记号】 |
【 分 子 式 】C31H36N2O7 【 分 子 量 】548.63612 【元素组成】C 67.87% H 6.61% N 5.11% O 20.41% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 5-methyluridine (I) with 1,1-dimethoxycyclopentane (II) by means of TsOH in hot dichloroethane gives the corresponding cyclic ketal (III), which is protected with 4-methoxybenzyl bromide and NaH in DME yielding the N,O-diprotected compound (IV). Elimination of the ketal protecting group of (IV) with dichloroacetic acid in water affords N3,O5'-bis(4-methoxybenzyl)-5-methyluridine (V), which is treated with PPh3, I2 and imidazole in hot toluene/acetonitrile to provide 2',3'-didehydro-2',3'-dideoxy-N3,O5’-bis(4-methoxybenzyl)-5-methyluridine (VI). Finally this compound is deprotected with ammonium cerium (IV) nitrate in acetonitrile/water.
| 【1】 Luzzio, F.A.; Menes, M.E.; A facile route to pyrimidine-based nuceloside olefins: Application to the synthesis of d4T(stavudine). J Org Chem 1994, 59, 24, 7267. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 41892 | 1,1-dimethoxycyclopentane; 1-methoxycyclopentyl methyl ether | 931-94-2 | C7H14O2 | 详情 | 详情 |
| (III) | 41893 | C15H20N2O6 | 详情 | 详情 | ||
| (IV) | 41894 | C31H36N2O7 | 详情 | 详情 | ||
| (V) | 41895 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(4-methoxyphenethyl)tetrahydro-2-furanyl]-3-(4-methoxybenzyl)-5-methyl-2,4(1H,3H)-pyrimidinedione | C26H30N2O7 | 详情 | 详情 | |
| (VI) | 41896 | 3-(4-methoxybenzyl)-1-[(2R,5R)-5-(4-methoxyphenethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | C26H28N2O5 | 详情 | 详情 |