(4R,5S,6S,8S,10R,11R,12R,13R)-5,13-di[tert-butyldimethylsilyloxy]-11-triethylsilyloxy-4,6,8,10,12,14-hexamethylpentadeca-3,7,9-trione | 888488-21-9

• 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: (4R,5S,6S,8S,10R,11R,12R,13R)-5,13-di[tert-butyldimethylsilyloxy]-11-triethylsilyloxy-4,6,8,10,12,14-hexamethylpentadeca-3,7,9-trione
• 英文别名: (4R,5S,6S,8S,10R,11R,12R,13R)-5,13-bis[[tert-butyl(dimethyl)silyl]oxy]-4,6,8,10,12,14-hexamethyl-11-triethylsilyloxypentadecane-3,7,9-trione
• CAS: 888488-21-9
• 化学式: C₃₉H₈₀O₆Si₃
• 分子量: 729.317
• InChiKey: YRFUEVVIPLRFEK-NTODPGRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.11
• 重原子数：
  48
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S,8S,10R,11R,12R,13R)-5,13-di[tert-butyldimethylsilyloxy]-11-triethylsilyloxy-4,6,8,10,12,14-hexamethylpentadeca-3,7,9-trione 在 氟化氢吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 168.0h， 以88%的产率得到5-[(1R,2S,3S,4R)-4-tert-butyldimethylsilyloxy-2-hydroxy-1,3,5-trimethylhexyl]-3-ethyl-8,9,10-trimethyl-2,4,6-trioxatricyclo[3.3.1.1(3,7)]decan-1-ol
  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：

  (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one 在 W-2 Raney nickel 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 samarium diiodide 、 草酰氯 、 三氟甲磺酸 、 氢气 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (4R,5S,6S,8S,10R,11R,12R,13R)-5,13-di[tert-butyldimethylsilyloxy]-11-triethylsilyloxy-4,6,8,10,12,14-hexamethylpentadeca-3,7,9-trione
  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

文献信息

• A Retro-Claisen Approach to Dolabriferol
  作者：Troy Lister、Michael V. Perkins

  DOI：10.1021/ol060347s

  日期：2006.4.1

  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.