5'-O-crotonylthymidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-crotonylthymidine
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (E)-but-2-enoate
• 化学式: C₁₄H₁₈N₂O₆
• 分子量: 310.307
• InChiKey: VENSHNMUBBRHOX-BJPDOBEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  vinyl crotonate 、 beta-胸苷 在 Candida antarctica lipase B 作用下， 以 四氢呋喃 为溶剂， 反应 43.0h， 以75%的产率得到5'-O-crotonylthymidine
  参考文献：
  名称：

  Novel and efficient regioselective enzymatic approach to 3′-, 5′- and 3′,5′-di-O-crotonyl 2′-deoxynucleoside derivatives

  摘要：

  Regioselective syntheses of several O-crotonyl 2'-deoxynucleoside derivatives have been efficiently achieved using a bio-catalytic methodology. While Candida antarctica lipase B (CAL-B) afforded the 5'-O-acylated compounds, immobilized lipase from Pseudomonas cepacia (PSL-C) provided the 3'-O-crotonylated analogs. Since classical chemical approaches did not work appropriately due to side isomerization reactions, a mixture of both lipases was used to achieve a useful synthetic route toward diacylated nucleosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.138

文献信息

• Novel and efficient regioselective enzymatic approach to 3′-, 5′- and 3′,5′-di-O-crotonyl 2′-deoxynucleoside derivatives
  作者：Alba Díaz-Rodríguez、Susana Fernández、Iván Lavandera、Miguel Ferrero、Vicente Gotor

  DOI：10.1016/j.tetlet.2005.06.138

  日期：2005.8

  Regioselective syntheses of several O-crotonyl 2'-deoxynucleoside derivatives have been efficiently achieved using a bio-catalytic methodology. While Candida antarctica lipase B (CAL-B) afforded the 5'-O-acylated compounds, immobilized lipase from Pseudomonas cepacia (PSL-C) provided the 3'-O-crotonylated analogs. Since classical chemical approaches did not work appropriately due to side isomerization reactions, a mixture of both lipases was used to achieve a useful synthetic route toward diacylated nucleosides. (c) 2005 Elsevier Ltd. All rights reserved.