(1S,4aS,5R,6R,8S,8aS)-1-Allyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol | 199525-24-1

• 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: (1S,4aS,5R,6R,8S,8aS)-1-Allyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol
• CAS: 199525-24-1
• 化学式: C₃₇H₅₈O₂Si₂
• 分子量: 591.037
• InChiKey: OPFNRYMTZWGWTF-DNZSARARSA-N

物化性质

• 沸点：
  581.926±46.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.001±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,4aS,5R,6R,8S,8aS)-1-Allyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol 在 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 三氟化硼 、 碘 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 23.67h， 生成
  参考文献：
  名称：

  Total Synthesis of Dysidiolide

  摘要：

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product. Once the central portion of 1 was established, elaboration of the side chains was accomplished expediently via steps that included (1) vinyl cuprate displacement of an iodide to complete the C-l side chain, (2) a highly diastereoselective oxazaborolidine-catalyzed (CBS) reduction to form carbinol 11, and (3) photochemical oxidation of 11 to generate the gamma-hydroxybutenolide functionality of 1. Additionally, this synthesis proves the absolute stereochemistry of dysidiolide (1).

  DOI：

  10.1021/ja973023v
• 作为产物：
  描述：

  (4aS,5S,8S,8aS)-5-(2-Hydroxy-ethyl)-5,8a-dimethyl-6-methylene-8-trimethylsilanyl-octahydro-naphthalen-1-one 在 Wilkinson's catalyst 2,6-二甲基吡啶 、 4-二甲氨基吡啶 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， -78.0~65.0 ℃ 、6.89 MPa 条件下， 反应 24.83h， 生成 (1S,4aS,5R,6R,8S,8aS)-1-Allyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol
  参考文献：
  名称：

  Total Synthesis of Dysidiolide

  摘要：

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product. Once the central portion of 1 was established, elaboration of the side chains was accomplished expediently via steps that included (1) vinyl cuprate displacement of an iodide to complete the C-l side chain, (2) a highly diastereoselective oxazaborolidine-catalyzed (CBS) reduction to form carbinol 11, and (3) photochemical oxidation of 11 to generate the gamma-hydroxybutenolide functionality of 1. Additionally, this synthesis proves the absolute stereochemistry of dysidiolide (1).

  DOI：

  10.1021/ja973023v