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【结 构 式】 
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【分子编号】41904 【品名】[(2R,3S,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3-(phenylselanyl)tetrahydro-2-furanyl]methyl benzoate 【CA登记号】 |
【 分 子 式 】C23H22N2O5Se 【 分 子 量 】485.39816 【元素组成】C 56.91% H 4.57% N 5.77% O 16.48% Se 16.27% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(IV)The benzoylation of thymidine (I) with benzoyl chloride, PPh3 and DIAD in THF gives the 5'-O-benzoylthymidine (II), which is converted into the anhydro compound (III) by reaction with PPh3 and DIAD in DMF. The reaction of (III) with PhSeH in refluxing DMF affords the phenylselenium derivative (IV), which is treated with H2O2 and HOAc in THF to provide the benzoylated anhydrothymidine (V). Finally this compound is debenzoylated by means of NaOMe in methanol.
| 【1】 Becouarn, S.; Czernecki, S.; Valery, J.-M.; Efficient transformation of thymidine into 2',3'-didehydro-2',3'-dideoxy-thymidine (D4T) involving opening of a 2,3'-anhydro derivative by phenylselenol. Nucleosides Nucleotides 1995, 14, 6, 1227. |
| 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) | 12161 | Thymidine; 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | 50-89-5 | C10H14N2O5 | 详情 | 详情 |
| (II) | 41902 | [(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate | C17H18N2O6 | 详情 | 详情 | |
| (III) | 41903 | [(1R,9S,10R)-4-methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.0(2,7)]dodeca-3,6-dien-10-yl]methyl benzoate | C17H16N2O5 | 详情 | 详情 | |
| (IV) | 41904 | [(2R,3S,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-3-(phenylselanyl)tetrahydro-2-furanyl]methyl benzoate | C23H22N2O5Se | 详情 | 详情 | |
| (V) | 12257 | 2,4,5-Trifluoro-3-methoxybenzamide | C8H6F3NO2 | 详情 | 详情 |
Extended Information