(E)-ethyl 3-((4S,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate | 914366-87-3

• 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,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate
• 英文别名: ethyl (E)-3-[(4S,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 914366-87-3
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: CCCMYNJKRJVAEB-HIGCGDNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 甲酸 、 potassium tert-butylate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.58h， 生成 ethyl 2-[(4S,5R,6R)-5,6-dimethyl-2-phenyl-1,3-dioxan-4-yl]acetate
  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：

  (E,4S,5R)-ethyl 4,5-dihydroxy-4-methylhex-2-enoate 、 三光气 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 (E)-ethyl 3-((4S,5R)-4,5-dimethyl-2-oxo-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).