(2E,8E)-(5R,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-deca-2,8-dienedioic acid dimethyl ester | 159292-69-0

• 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: (2E,8E)-(5R,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-deca-2,8-dienedioic acid dimethyl ester
• CAS: 159292-69-0
• 化学式: C₂₄H₄₆O₆Si₂
• 分子量: 486.797
• InChiKey: DXLKMUXHWXSDFL-QDZOKRIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2E,8E)-(5R,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-deca-2,8-dienedioic acid dimethyl ester 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以100%的产率得到(5R,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-decanedioic acid dimethyl ester
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034
• 作为产物：
  描述：

  三甲基膦酰基乙酸酯 、 (3R*,4S*)-3,4-bis(tert-butyldimethylsilyloxy)hexanedial 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 0.5h， 以83%的产率得到(2E,8E)-(5R,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-deca-2,8-dienedioic acid dimethyl ester
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034