(1R,2S,5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclooctane-1,2-diol | 159292-75-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2S,5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclooctane-1,2-diol
• CAS: 159292-75-8
• 化学式: C₂₀H₄₄O₄Si₂
• 分子量: 404.738
• InChiKey: DLMKJOPRWHNZBW-USTZCAOPSA-N

物化性质

• 沸点：
  412.6±45.0 °C(predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclooctane-1,2-diol 在 platinum(IV) oxide sodium periodate 、 氢气 、 sodium hydride 作用下， 以 水 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 5.5h， 生成 dimethyl (6R,7S)-6,7-bis[[tert-butyl(dimethyl)silyl]oxy]dodecanedioate
  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：

  (5R*,6S*)-5,6-bis(tert-butyldimethylsilyloxy)cyclooctene 在 四氧化锇 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.0h， 以97%的产率得到(1R,2S,5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclooctane-1,2-diol
  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