(E)-ethyl 3-((4S,5S)-4-methyl-2-oxo-5-phenyl-1,3-dioxolan-4-yl)acrylate | 914366-82-8

• 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: (E)-ethyl 3-((4S,5S)-4-methyl-2-oxo-5-phenyl-1,3-dioxolan-4-yl)acrylate
• 英文别名: ethyl (E)-3-[(4S,5S)-4-methyl-2-oxo-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 914366-82-8
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: BGBNMUCORHGORQ-IXLVIVEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-ethyl 3-((4S,5S)-4-methyl-2-oxo-5-phenyl-1,3-dioxolan-4-yl)acrylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 甲酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 Ethyl (+/-)-(E)-(4R^*,5S^*)-5-hydroxy-4-methyl-5-phenyl-2-pentenoate
  参考文献：
  名称：

  De Novo Synthesis of 2-Substituted syn-1,3-Diols via an Iterative Asymmetric Hydration Strategy

  摘要：

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).

  DOI：

  10.1021/jo061200h
• 作为产物：
  描述：

  反式-alpha-甲基肉桂醛 在 甲基磺酰胺 、 potassium carbonate 吡啶 、 四氧化锇 、 DHQ-2-Me-2-Quin 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 8.08h， 生成 (E)-ethyl 3-((4S,5S)-4-methyl-2-oxo-5-phenyl-1,3-dioxolan-4-yl)acrylate
  参考文献：
  名称：

  De Novo Synthesis of 2-Substituted syn-1,3-Diols via an Iterative Asymmetric Hydration Strategy

  摘要：

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).

  DOI：

  10.1021/jo061200h

文献信息

• De Novo Synthesis of 2-Substituted <i>syn</i>-1,3-Diols via an Iterative Asymmetric Hydration Strategy
  作者：Md. Moinuddin Ahmed、Matthew S. Mortensen、George A. O'Doherty

  DOI：10.1021/jo061200h

  日期：2006.9.1

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).