1-[5-ethynyl-3,4-dihydroxy-tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione | 64189-21-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-[5-ethynyl-3,4-dihydroxy-tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-(6-Deoxy-β-D-ribo-hex-5-ynofuranosyl)uracil；1-(β-D-ribo-5,6-dideoxy-hex-5-ynofuranosyl)-1H-pyrimidine-2,4-dione；1-(5,6-Dideoxy-β-D-ribo-hex-5-ynofuranosyl)-uracil
• CAS: 64189-21-5
• 化学式: C₁₀H₁₀N₂O₅
• 分子量: 238.2
• InChiKey: RRCFOMFOABXVGM-ZOQUXTDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.21
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104.55
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[5-ethynyl-3,4-dihydroxy-tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione 在 吡啶 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 18.0h， 生成 1-(5-ethynylfuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy-5′-norarabinouridine: a new anti-HIV nucleoside analogue

  摘要：

  3'-Azido-4'-ethynyl-3',5'dideoxy-5'-norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2',3'-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.054
• 作为产物：
  描述：

  1-(2',3'-O-isopropylidene-5',6'-dideoxy-6',6'-dibromo-β-D-ribo-5'-hexenofuranosyl)uracil 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 生成 1-[5-ethynyl-3,4-dihydroxy-tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy-5′-norarabinouridine: a new anti-HIV nucleoside analogue

  摘要：

  3'-Azido-4'-ethynyl-3',5'dideoxy-5'-norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2',3'-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.054

文献信息

• Nucleic acid related compounds. 78. Stereocontrolled syntheses of 6′(<i>E</i> and <i>Z</i>)-halovinyl analogues from uridine-derived vinylsulfones via vinyltin intermediates
  作者：Stanislaw F. Wnuk、Morris J. Robins

  DOI：10.1139/v93-028

  日期：1993.2.1

  Treatment of the 6′(E)-tosylvinyl homonucleoside 1a with Bu3SnH/AIBN/toluene/Δ gave separable mixtures of 6′-vinylstannanes 2a(E/Z) in high yields. Stereospecific halodestannylations with N-iodosuccinimide, bromine, and N-bromosuccinimide proceeded smoothly to give the 6′(E or Z)-iodo(and bromo) vinyl compounds with retention of configuration. Chlorine or iodobenzene dichloride effected moderately

  用 Bu3SnH/AIBN/甲苯/Δ 处理 6'(E)-甲苯磺酰基乙烯基同核苷 1a，以高产率得到 6'-乙烯基锡烷 2a(E/Z) 的可分离混合物。N-碘代琥珀酰亚胺、溴和 N-溴代琥珀酰亚胺的立体特异性卤代脱烷基化顺利进行，得到 6'（E 或 Z）-碘（和溴）乙烯基化合物，并保留构型。氯或碘苯二氯化物实现适度立体选择性的氯去甲酰化。用 NH4F/MeOH/Δ 处理 2a 导致碳-锡键断裂，得到游离的乙烯基衍生物 4a。三氟乙酸水溶液同时实现了 2a 的蛋白脱乙酰基化和脱保护，得到 4b。用四乙酸铅/乙腈处理2a(E)并脱保护得到炔衍生物3b。