(4S,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-difluoro-ethyl]-4-isobutyl-oxazolidin-2-one | 147092-78-2

• 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-silanyloxy)-1,1-difluoro-ethyl]-4-isobutyl-oxazolidin-2-one
• 英文别名: (4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-difluoroethyl]-4-(2-methylpropyl)-1,3-oxazolidin-2-one
• CAS: 147092-78-2
• 化学式: C₁₅H₂₉F₂NO₃Si
• 分子量: 337.482
• InChiKey: YVOGPZFSRYZUKW-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 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：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-difluoro-ethyl]-4-isobutyl-oxazolidin-2-one 在 jones reagent 作用下， 生成 (3R,4S)-4-tert-Butoxycarbonylamino-2,2-difluoro-3-hydroxy-6-methyl-heptanoic acid methyl ester
  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-difluoroethyl]-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-silanyloxy)-1,1-difluoro-ethyl]-4-isobutyl-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.