(4R,5R,6R,7R)-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one | 888488-08-2

• 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: (4R,5R,6R,7R)-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one
• 英文别名: (4R,5R,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4,6,8-trimethyl-5-triethylsilyloxynonan-3-one
• CAS: 888488-08-2
• 化学式: C₂₄H₅₂O₃Si₂
• 分子量: 444.846
• InChiKey: ZLYBPKYEZMPDNK-JVSAHFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R,6R,7R)-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one 在 草酰氯 、 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 、 二氯甲烷 为溶剂， 反应 3.5h， 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
• 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 、 二甲基十二/十四烷基叔胺 、 氯代二环己基硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (4R,5R,6R,7R)-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one
  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.