ethyl 3-((3S,4aR,5R,6S,8aS)-3,6-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-hydroxypropanoate | 1338724-27-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 3-((3S,4aR,5R,6S,8aS)-3,6-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-hydroxypropanoate
• CAS: 1338724-27-8
• 化学式: C₃₇H₇₄O₆Si₃
• 分子量: 699.247
• InChiKey: RLRDQTBHPHQIPG-MQWPJKTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.25
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-((3S,4aR,5R,6S,8aS)-3,6-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-hydroxypropanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以186 mg的产率得到(Z)-ethyl 3-((3S,4aR,5R,6S,8aS)-3,6-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-hydroxyacrylate
  参考文献：
  名称：

  Total synthesis of pyripyropene A

  摘要：

  The total synthesis of pyripyropene A, a potent ACAT2 inhibitor with high isozyme selectivity, was completed. Key features of the synthetic strategy include Ti(III)-mediated radical cyclization and Peterson olefination for the construction of the AB ring segment and stereoselective dihydro-gamma-pyrone formation (C-ring). The total synthesis provided pyripyropene A in 5.3% overall yield over 17 steps. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.084
• 作为产物：
  描述：

  (4aS,5R,6S,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 在 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 仲丁基锂 、 potassium carbonate 、 溶剂黄146 、 lithium hexamethyldisilazane 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 ethyl 3-((3S,4aR,5R,6S,8aS)-3,6-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-hydroxypropanoate
  参考文献：
  名称：

  Total synthesis of pyripyropene A

  摘要：

  The total synthesis of pyripyropene A, a potent ACAT2 inhibitor with high isozyme selectivity, was completed. Key features of the synthetic strategy include Ti(III)-mediated radical cyclization and Peterson olefination for the construction of the AB ring segment and stereoselective dihydro-gamma-pyrone formation (C-ring). The total synthesis provided pyripyropene A in 5.3% overall yield over 17 steps. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.084