ditert-butyl (2S)-2-hydroxy-2-[(3R,5S)-5-phenyloxolan-3-yl]butanedioate | 1353720-81-6

• 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: ditert-butyl (2S)-2-hydroxy-2-[(3R,5S)-5-phenyloxolan-3-yl]butanedioate
• CAS: 1353720-81-6
• 化学式: C₂₂H₃₂O₆
• 分子量: 392.492
• InChiKey: FLDHGTVWQMQMRW-JLHGSKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S)-2-hydroxy-2-[(3R,5S)-5-phenyloxolan-3-yl]butanedioate 在 copper(II) bis(trifluoromethanesulfonate) 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  A Stereoselective Synthesis of (−)-Viridiofungin A Utilizing a TiCl₄-Promoted Asymmetric Multicomponent Reaction

  摘要：

  A stereoselective synthesis of (-)-viridiofungin A is described. The convergent synthesis utilized a unique highly diastereoselective multicomponent reaction between optically active phenyldihydrofuran and an beta-ketoester to provide two chiral centers including a quarternary carbon center in a single step. Other key steps include an acyloxycarbonium ion-mediated tetrahydrofuran ring-opening reaction and a Julia-Kocienski olefination.

  DOI：

  10.1021/ol203093g
• 作为产物：
  描述：

  (S)-2-phenyl-2,3-dihydrofuran 在 硼烷四氢呋喃络合物 、 水 、 四氯化钛 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 ditert-butyl (2S)-2-hydroxy-2-[(3R,5S)-5-phenyloxolan-3-yl]butanedioate
  参考文献：
  名称：

  A Stereoselective Synthesis of (−)-Viridiofungin A Utilizing a TiCl₄-Promoted Asymmetric Multicomponent Reaction

  摘要：

  A stereoselective synthesis of (-)-viridiofungin A is described. The convergent synthesis utilized a unique highly diastereoselective multicomponent reaction between optically active phenyldihydrofuran and an beta-ketoester to provide two chiral centers including a quarternary carbon center in a single step. Other key steps include an acyloxycarbonium ion-mediated tetrahydrofuran ring-opening reaction and a Julia-Kocienski olefination.

  DOI：

  10.1021/ol203093g

文献信息

• A Stereoselective Synthesis of (−)-Viridiofungin A Utilizing a TiCl₄-Promoted Asymmetric Multicomponent Reaction
  作者：Arun K. Ghosh、Jorden Kass

  DOI：10.1021/ol203093g

  日期：2012.1.20

  A stereoselective synthesis of (-)-viridiofungin A is described. The convergent synthesis utilized a unique highly diastereoselective multicomponent reaction between optically active phenyldihydrofuran and an beta-ketoester to provide two chiral centers including a quarternary carbon center in a single step. Other key steps include an acyloxycarbonium ion-mediated tetrahydrofuran ring-opening reaction and a Julia-Kocienski olefination.