ethyl (2Z,4S,5R)-4,5-bis(benzyloxy)-6-oxohex-2-enoate | 1443524-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (2Z,4S,5R)-4,5-bis(benzyloxy)-6-oxohex-2-enoate
• 英文别名: ethyl (Z,4S,5R)-6-oxo-4,5-bis(phenylmethoxy)hex-2-enoate
• CAS: 1443524-06-8
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: JOTSTRJEIFGNEO-JWWMHJHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,4S,5R)-4,5-bis(benzyloxy)-6-oxohex-2-enoate 在 甲醇 、 lithium aluminium tetrahydride 、 2-硝基苯基丝氰酸酯 、 samarium diiodide 、 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.84h， 生成 (1R,2S,3S,4R)-2,3-bis(benzyloxy)-4-vinylcyclobutanol
  参考文献：
  名称：

  Synthesis of 4-Membered Carbasugars by Way of Stereoselective SmI₂-Mediated Aldehyde–Alkene Cyclization

  摘要：

  A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.

  DOI：

  10.1021/jo400732a
• 作为产物：
  描述：

  ethyl (4S,5S)-4,5-bis(benzyloxy)-6-hydroxyhex-2-enoate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以33.333%的产率得到
  参考文献：
  名称：

  Synthesis of 4-Membered Carbasugars by Way of Stereoselective SmI₂-Mediated Aldehyde–Alkene Cyclization

  摘要：

  A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.

  DOI：

  10.1021/jo400732a

文献信息

• Synthesis of 4-Membered Carbasugars by Way of Stereoselective SmI₂-Mediated Aldehyde–Alkene Cyclization
  作者：Pierre-Antoine Nocquet、Damien Hazelard、Guillaume Gruntz、Philippe Compain

  DOI：10.1021/jo400732a

  日期：2013.7.5

  A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.