methyl (Z)-4-(5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene)butanoate | 1040754-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: methyl (Z)-4-(5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene)butanoate
• CAS: 1040754-33-3
• 化学式: C₁₈H₂₃N₅O₅
• 分子量: 389.411
• InChiKey: ARORMKAEPXZQRY-JRBQZKQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  123.61
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-4-(5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene)butanoate 在 水 、 三氟乙酸 作用下， 反应 1.0h， 以56%的产率得到methyl (Z)-4-(5'-deoxyadenosin-5'-ylidene)butanoate
  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：

  甲醇 、 在 氨 作用下， 以35 mg的产率得到methyl (Z)-4-(5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene)butanoate
  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