(3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione | 888488-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione
• CAS: 888488-07-1
• 化学式: C₄₇H₉₀O₇Si₃
• 分子量: 851.484
• InChiKey: NHOITWYBYJCXCF-IEOWHBDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.14
• 重原子数：
  57.0
• 可旋转键数：
  25.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(3R,4S,5R,6R,8S,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-2,4,6,8,10,12-hexamethyl-5-hydroxy-13-[4-methoxybenzyloxy]pentadeca-7,9-dione
  参考文献：
  名称：

  A Retro-Claisen Approach to Dolabriferol

  摘要：

  The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

  DOI：

  10.1021/ol060347s
• 作为产物：
  描述：

  (2R,3R)-2,4-dimethyl-3-[(tert-butyldimethylsilyl)oxy]pentanal 在 2,6-二甲基吡啶 、 samarium diiodide 、 草酰氯 、 二甲基十二/十四烷基叔胺 、 氯代二环己基硼烷 、 二甲基亚砜 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione
  参考文献：
  名称：

  A Retro-Claisen Approach to Dolabriferol

  摘要：

  The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

  DOI：

  10.1021/ol060347s