ethyl (E)-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-methylsulfanylcarbothioyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylpent-2-enoate | 144677-74-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-methylsulfanylcarbothioyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylpent-2-enoate
• CAS: 144677-74-7
• 化学式: C₁₇H₂₆O₆S₂
• 分子量: 390.522
• InChiKey: HOFSFOOEXXZKKB-IVYHSSSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-methylsulfanylcarbothioyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylpent-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以83%的产率得到(1S,2R,6R,8R,11S)-4,4-dimethyl-N-phenylmethoxy-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-11-amine
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8
• 作为产物：
  描述：

  ethyl 5,6-dideoxy-1,2-O-isopropylidene-3-O-(S-methyl-thiocarbonate)-α-D-xylo-hepto-furanuronate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.5h， 生成 ethyl (E)-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-methylsulfanylcarbothioyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylpent-2-enoate
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8

文献信息

• Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates
  作者：José Marco-Contelles、Pilar Ruiz、Luis Martínez、Angeles Martínez-Grau

  DOI：10.1016/s0040-4020(01)81837-8

  日期：1993.7

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.