(E,4S,5S)-ethyl 7-(tert-butyldimethylsilyloxy)-4,5-dihydroxy-4-methylhept-2-enoate | 914366-67-9

• 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,4S,5S)-ethyl 7-(tert-butyldimethylsilyloxy)-4,5-dihydroxy-4-methylhept-2-enoate
• 英文别名: ethyl (E,4S,5S)-7-[tert-butyl(dimethyl)silyl]oxy-4,5-dihydroxy-4-methylhept-2-enoate
• CAS: 914366-67-9
• 化学式: C₁₆H₃₂O₅Si
• 分子量: 332.513
• InChiKey: GOODFXWSFBYQRR-XXKLSNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,4S,5S)-ethyl 7-(tert-butyldimethylsilyloxy)-4,5-dihydroxy-4-methylhept-2-enoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 甲酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E,4S,5S)-ethyl 7-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methylhept-2-enoate
  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：

  (2E,4E)-ethyl 7-(tert-butyldimethylsilyloxy)-4-methylhepta-2,4-dienoate 在 四氧化锇 Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (E,4S,5S)-ethyl 7-(tert-butyldimethylsilyloxy)-4,5-dihydroxy-4-methylhept-2-enoate 、 (E,4R,5R)-ethyl 7-(tert-butyldimethylsilyloxy)-4,5-dihydroxy-4-methylhept-2-enoate
  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).