(1S,4aS,5R,6R,8S,8aS)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(3-hydroxy-propyl)-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol | 199525-25-2

• 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)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(3-hydroxy-propyl)-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol
• CAS: 199525-25-2
• 化学式: C₃₇H₆₀O₃Si₂
• 分子量: 609.053
• InChiKey: ISEHLYWPCKTADE-RKVHFZCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,4aS,5R,6R,8S,8aS)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(3-hydroxy-propyl)-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol 在 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼 、 四丁基氟化铵 、 碘 、 叔丁基锂 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 31.34h， 生成 (1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-keto-2-(3-furyl)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene
  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：

  (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 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到(1S,4aS,5R,6R,8S,8aS)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(3-hydroxy-propyl)-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