(2'S,3'R,4S,4'E)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-2'-ethenyl-3'-hydroxy-4'-pentenoyl]-oxazolidin-2-one | 251908-41-5

• 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: (2'S,3'R,4S,4'E)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-2'-ethenyl-3'-hydroxy-4'-pentenoyl]-oxazolidin-2-one
• CAS: 251908-41-5
• 化学式: C₂₂H₃₁NO₄Si
• 分子量: 401.578
• InChiKey: FEXLKEVIWCAYBE-FBHZQTJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'R,4S,4'E)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-2'-ethenyl-3'-hydroxy-4'-pentenoyl]-oxazolidin-2-one 反应 8.0h， 以60%的产率得到(2'E,4S,5'S)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-7'-oxo-2'-heptenoyl]-oxazolidin-2-one
  参考文献：
  名称：

  General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

  摘要：

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7
• 作为产物：
  描述：

  (E)-3-(Dimethylphenylsilyl)-2-propenal 、 (S,E)‐3‐(but‐2‐enoyl)‐4‐(tert‐butyl)oxazolidin‐2‐one 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以82%的产率得到(2'S,3'R,4S,4'E)-4-tert-Butyl-3-[5'-dimethylphenylsilyl-2'-ethenyl-3'-hydroxy-4'-pentenoyl]-oxazolidin-2-one
  参考文献：
  名称：

  General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

  摘要：

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7

文献信息

• General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups
  作者：Christoph Schneider、Markus Rehfeuter

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2850::aid-chem2850>3.0.co;2-7

  日期：1999.10.1

  A stereoselective synthesis of enantiomerically purl 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operations-an allylboration, an oxidative desilylation, and a conjugate addition reaction-were employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.