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【结 构 式】 
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【分子编号】42586 【品名】5-(1-decynyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C19H28N2O5 【 分 子 量 】364.4418 【元素组成】C 62.62% H 7.74% N 7.69% O 21.95% |
合成路线1
该中间体在本合成路线中的序号：(III)Coupling of 5-iodo-2'-deoxyuridine (I) with 1-decyne (II) in the presence of cuprous iodide and tetrakis(triphenylphosphine)palladium furnished the 5-decynyl uridine derivative (III). This was then cyclized to the title furopyrimidinone by treatment with cuprous iodide and triethylamine in refluxing methanol.
| 【1】 Balzarini, J.; McGuigan, C.; Andrei, G.; Srinivasan, S.; Snoeck, R.; De clercq, E.; Bicyclic nucleoside inhibitors of varicella-Zoster virus (VZV): The effect of terminal unsaturation in the side chain. Bioorg Med Chem Lett 2001, 11, 3, 391. |
| 【2】 Brancale, A.; Snoeck, R.; Yarnold, C.J.; Barucki, H.; Velázquez, S.; Jones, G.; Andrei, G.; McGuigan, C.; De Clercq, E.; Balzarini, J.; Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. J Med Chem 1999, 42, 22, 4479. |
| 【3】 Jones, G.; Balzarini, J.; McGuigan, C.; Yarnold, C.; De Clercq, E. (University College, Cardiff); Anti-viral pyrimidine nucleoside analogues. EP 0980377; WO 9849177 . |
| 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) | 42585 | 1-decyne | 764-93-2 | C10H18 | 详情 | 详情 |
| (III) | 42586 | 5-(1-decynyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C19H28N2O5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The known 5-decynyl-2'-deoxyuridine (I) was protected as the bis-silyl ether (II) with chlorotrimethylsilane and triethylamine. Treatment of (II) with POCl3 and triazole produced the triazolyl derivative (III). Finally, reaction of (III) with thioacetic acid gave rise to the desired thienopyrimidine.
| 【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 |
|---|---|---|---|---|---|---|
| (I) | 42586 | 5-(1-decynyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C19H28N2O5 | 详情 | 详情 | |
| (II) | 52280 | 5-(1-decynyl)-1-(4-[(trimethylsilyl)oxy]-5-{[(trimethylsilyl)oxy]methyl}tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione | C25H44N2O5Si2 | 详情 | 详情 | |
| (III) | 52281 | 5-(1-decynyl)-4-(1H-1,2,4-triazol-1-yl)-1-(4-[(trimethylsilyl)oxy]-5-{[(trimethylsilyl)oxy]methyl}tetrahydro-2-furanyl)-2(1H)-pyrimidinone | C27H45N5O4Si2 | 详情 | 详情 |