(4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-dichloroethyl]-4-(2-methylpropyl)-1,3-oxazolidin-2-one | 147092-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-dichloroethyl]-4-(2-methylpropyl)-1,3-oxazolidin-2-one
• CAS: 147092-77-1
• 化学式: C₁₅H₂₉Cl₂NO₃Si
• 分子量: 370.392
• InChiKey: VNKBMWILTKSYES-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-dichloroethyl]-4-(2-methylpropyl)-1,3-oxazolidin-2-one 在 jones reagent 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 二丁基锡烷 作用下， 生成 (3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate
  参考文献：
  名称：

  Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs

  摘要：

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.

  DOI：

  10.1021/jo00060a006
• 作为产物：
  描述：

  (4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-dichloroethyl]-4-methoxy-1,3-oxazolidin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟化硼乙醚 作用下， 生成 (4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-dichloroethyl]-4-(2-methylpropyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs

  摘要：

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.

  DOI：

  10.1021/jo00060a006

文献信息

• Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs
  作者：Takuya Yamamoto、Seigo Ishibuchi、Tadao Ishizuka、Mamoru Haratake、Takehisa Kunieda

  DOI：10.1021/jo00060a006

  日期：1993.4

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.