(1S*,2S*,5R*,6R*,7S*,8R*)-8-(tert-Butyldimethylsiloxy)-2,5-diiodo-9-oxabicyclo<4.2.1>nonan-7-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S*,2S*,5R*,6R*,7S*,8R*)-8-(tert-Butyldimethylsiloxy)-2,5-diiodo-9-oxabicyclo<4.2.1>nonan-7-ol
• 英文别名: (1S*,2S*,5R*,6R*,7S*,8R*)-8-(tert-Butyldimethylsiloxy)-2,5-diiodo-9-oxabicyclo[4.2.1]nonan-7-ol
• 化学式: C₁₄H₂₆I₂O₃Si
• 分子量: 524.253
• InChiKey: SZFXWLFHGBJNSK-JIMTYQMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S*,2S*,5R*,6R*,7S*,8R*)-8-(tert-Butyldimethylsiloxy)-2,5-diiodo-9-oxabicyclo<4.2.1>nonan-7-ol 在 tetraphenylporphyrin 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 草酰氯 、 四丁基氟化铵 、 氧气 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 70.83h， 生成 meso-2,7-Bis<(tert-butyldimethylsiloxy)methyl>-3,6-epidioxy-4,5-didehydrooxepane
  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：

  (Z,Z)-2,6-Cyclooctadien-1-ol 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 、 sodium hydroxide 、 pyridine-SO3 complex 、 dimethyl sulfide borane 、 双氧水 、 碘 、 三乙胺 作用下， 以 异辛烷 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 39.0h， 生成 (1S*,2S*,5R*,6R*,7S*,8R*)-8-(tert-Butyldimethylsiloxy)-2,5-diiodo-9-oxabicyclo<4.2.1>nonan-7-ol
  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

文献信息

• 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
  作者：Eleuterio Alvarez、Maria T. Diaz、Ricardo Perez、Jose L. Ravelo、Alicia Regueiro、Jose A. Vera、Dacil Zurita、Julio D. Martin

  DOI：10.1021/jo00089a034

  日期：1994.5

  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.