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【结 构 式】 
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【分子编号】52286 【品名】2-[(acetyloxy)methyl]-5-[6-octyl-2-oxothieno[2,3-d]pyrimidin-3(2H)-yl]tetrahydro-3-furanyl acetate 【CA登记号】 |
【 分 子 式 】C23H32N2O6S 【 分 子 量 】464.58296 【元素组成】C 59.46% H 6.94% N 6.03% O 20.66% S 6.9% |
合成路线1
该中间体在本合成路线中的序号：(IX)In another synthetic route, the starting 3',5'-di-O-acetyl-5-iodo-2'-deoxyuridine (IV) was converted to the corresponding 4-thio derivative (V) upon treatment with P2S5. This was S-methylated with iodomethane and triethylamine to give the 4-methylthio pyrimidinone (VI). Palladium-catalyzed coupling of this 5-iodopyrimidine (VI) with 1-decyne (VII) furnished the 5-decynyl nucleoside (VIII). Removal of the methylthio group with NaSH in DMF gave directly the cyclized thienopyrimidine (IX). The remaining acetate esters were finally hydrolyzed by treatment with a methanolic solution of ammonium hydroxide.
| 【1】 Brancale, A.; et al.; Bicyclic anti-VZV nucleosides: Thieno analogues retain full antiviral activity. Bioorg Med Chem Lett 2001, 11, 18, 2507. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 52282 | {3-(acetyloxy)-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate | C13H15IN2O7 | 详情 | 详情 | |
| (V) | 52283 | {3-(acetyloxy)-5-[5-iodo-2-oxo-4-thioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate | C13H15IN2O6S | 详情 | 详情 | |
| (VI) | 52284 | {3-(acetyloxy)-5-[5-iodo-4-(methylsulfanyl)-2-oxo-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate | C14H17IN2O6S | 详情 | 详情 | |
| (VII) | 42585 | 1-decyne | 764-93-2 | C10H18 | 详情 | 详情 |
| (VIII) | 52285 | {3-(acetyloxy)-5-[5-(1-decynyl)-4-(methylsulfanyl)-2-oxo-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate | C24H34N2O6S | 详情 | 详情 | |
| (IX) | 52286 | 2-[(acetyloxy)methyl]-5-[6-octyl-2-oxothieno[2,3-d]pyrimidin-3(2H)-yl]tetrahydro-3-furanyl acetate | C23H32N2O6S | 详情 | 详情 |