ethyl (E)-5-(5'-deoxy-2',3'-O-isopropylideneuridin-5'-ylidene)pentanoate | 1040754-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl (E)-5-(5'-deoxy-2',3'-O-isopropylideneuridin-5'-ylidene)pentanoate
• CAS: 1040754-42-4
• 化学式: C₁₉H₂₆N₂O₇
• 分子量: 394.425
• InChiKey: XJSJKODEPPGZAG-RQECHFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5-(5'-deoxy-2',3'-O-isopropylideneuridin-5'-ylidene)pentanoate 在 水 、 三氟乙酸 作用下， 反应 1.0h， 以72%的产率得到ethyl (E)-5-(5'-deoxyuridin-5'-ylidene)pentanoate
  参考文献：
  名称：

  Synthesis of 5′-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5′ and sulfur atoms replaced by a vinyl or halovinyl unit

  摘要：

  Adenosine and uridine analogues functionalized with alkenyl or. uoroalkenyl chain at C5' were prepared employing cross-metathesis, Negishi couplings, and Wittig reactions. Metathesis of the protected 5'-deoxy-5'- methyleneadenosine or uridine analogues with six-carbon amino acids (homoallylglycines) in the presence of Grubbs catalysts gave nucleoside analogues with the C5'-C6' double bond. Alternatively, the Pd-catalyzed cross-coupling between the protected 5'-deoxy-5'-(iodomethylene) nucleosides and suitable alkylzinc bromides also provided analogues with alkenyl unit. Stereoselective Pd-catalyzed monoalkylation of 5'-(bromofluoromethylene)-5'-deoxyadenosine with alkylzinc bromides afforded adenosylhomocysteine analogues with a 6'-(fluoro) vinyl motif. The vinylic adenine nucleosides produced time-dependent inactivation of the S-adenosyl-L-homocysteine hydrolases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.017
• 作为产物：
  描述：

  bromo(4-ethoxy-4-oxobutyl)zinc 、 1-<5,6-Dideoxy-6(E)-iodo-2,3-isopropylidene-β-D-ribo-hex-5-enofuranosyl>uracil 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.0h， 以72%的产率得到ethyl (E)-5-(5'-deoxy-2',3'-O-isopropylideneuridin-5'-ylidene)pentanoate
  参考文献：
  名称：

  Synthesis of 5′-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5′ and sulfur atoms replaced by a vinyl or halovinyl unit

  摘要：

  Adenosine and uridine analogues functionalized with alkenyl or. uoroalkenyl chain at C5' were prepared employing cross-metathesis, Negishi couplings, and Wittig reactions. Metathesis of the protected 5'-deoxy-5'- methyleneadenosine or uridine analogues with six-carbon amino acids (homoallylglycines) in the presence of Grubbs catalysts gave nucleoside analogues with the C5'-C6' double bond. Alternatively, the Pd-catalyzed cross-coupling between the protected 5'-deoxy-5'-(iodomethylene) nucleosides and suitable alkylzinc bromides also provided analogues with alkenyl unit. Stereoselective Pd-catalyzed monoalkylation of 5'-(bromofluoromethylene)-5'-deoxyadenosine with alkylzinc bromides afforded adenosylhomocysteine analogues with a 6'-(fluoro) vinyl motif. The vinylic adenine nucleosides produced time-dependent inactivation of the S-adenosyl-L-homocysteine hydrolases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.017