ethyl (4S,5R)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolane-4-carboxylate | 849775-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (4S,5R)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolane-4-carboxylate
• 英文别名: (2S,3R)-ethyl 2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolane-4-carboxylate；ethyl (4S,5R)-2,2-dimethyl-5-[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]-1,3-dioxolane-4-carboxylate
• CAS: 849775-41-3
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: XARUMRAWKIXPIV-ZDCRXTMVSA-N

物化性质

• 沸点：
  318.9±42.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (4S,5R)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolane-4-carboxylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以93%的产率得到((4R,5S)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Anamarine and Its Analogues

  摘要：

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

  DOI：

  10.1021/jo051681p
• 作为产物：
  描述：

  山梨酸乙酯 在 甲基磺酰胺 、 potassium hexacyanoferrate(III) 四氧化锇 、 (DHQ)2-PHAL 、 camphor-10-sulfonic acid 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 36.0h， 生成 ethyl (4S,5R)-2,2-dimethyl-5-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Anamarine and Its Analogues

  摘要：

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

  DOI：

  10.1021/jo051681p

文献信息

• De Novo Asymmetric Synthesis of Anamarine and Its Analogues
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/jo051681p

  日期：2005.11.1

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.
• Enantioselective Synthesis of 10-<i>e</i><i>pi</i>-Anamarine via an Iterative Dihydroxylation Sequence
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/ol047322i

  日期：2005.3.1

  The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.