(4R,5R,7R)-7-(tert-butyl-dimethyl-silyloxy)-4,5-dihydroxy-oct-2-enoic acid methyl ester | 485323-93-1

• 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: (4R,5R,7R)-7-(tert-butyl-dimethyl-silyloxy)-4,5-dihydroxy-oct-2-enoic acid methyl ester
• 英文别名: methyl (E,4R,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4,5-dihydroxyoct-2-enoate
• CAS: 485323-93-1
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: CJMKOAUJYXWOAR-UVPOXWBHSA-N

物化性质

• 沸点：
  392.0±42.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (4R,5R,7R)-7-(tert-butyl-dimethyl-silyloxy)-4,5-dihydroxy-oct-2-enoic acid methyl ester 在 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl (E)-3-[(4R,5R)-5-[(2R)-2-hydroxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
  参考文献：
  名称：

  A Short and Enantioselective Synthesis of Colletodiol

  摘要：

  以交叉耦合偏析和 Sharpless 二羟基化反应为关键步骤，实现了 12 步对映体选择性合成可乐定。

  DOI：

  10.1055/s-2005-871562
• 作为产物：
  描述：

  (7R)-7-hydroxy-octa-2,4-dienoic acid methyl ester 在 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 4-二甲氨基吡啶 、 甲基磺酰胺 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (4R,5R,7R)-7-(tert-butyl-dimethyl-silyloxy)-4,5-dihydroxy-oct-2-enoic acid methyl ester
  参考文献：
  名称：

  Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.

  DOI：

  10.1021/ol0269502

文献信息

• Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A
  作者：Thomas J. Hunter、George A. O'Doherty

  DOI：10.1021/ol0269502

  日期：2002.12.1

  [GRAPHICS]The enantioselective synthesis of colletodiol has been achieved in 11 steps from methyl 1,3,5-octatrienoate and 16 total steps from both ethyl sorbate and methyl 1,3,5-octatrienoate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a 5-hydroxy-1-enoate and an 7-hydroxy-1,3-dienoate. These esters were further functionalized, coupled, and macrolactonized to provide colletodiol after deprotection. Grahamimycin A and colletol were synthesized in one and two steps, respectively, from colletodiol.
• A Short and Enantioselective Synthesis of Colletodiol
  作者：Janine Cossy、Laurent Ferrié、Patrice Capdevielle

  DOI：10.1055/s-2005-871562

  日期：——

  A 12-step enantioselective synthesis of colletodiol has been achieved using a cross-coupling metathesis and a Sharpless ­dihydroxylation as the key steps.

  以交叉耦合偏析和 Sharpless 二羟基化反应为关键步骤，实现了 12 步对映体选择性合成可乐定。