(S)-2,2,2-trichloroethyl 4-(((1R,2S,3S,6R)-3-acetoxy-2-hydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 1202810-37-4

• 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: (S)-2,2,2-trichloroethyl 4-(((1R,2S,3S,6R)-3-acetoxy-2-hydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: 2,2,2-trichloroethyl (4S)-4-[[(1R,2S,3S,6R)-3-acetyloxy-2-hydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1202810-37-4
• 化学式: C₁₇H₂₂Cl₃NO₇
• 分子量: 458.723
• InChiKey: CLAYQHQCQAWKGQ-SMTWKSNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-2,2,2-trichloroethyl 4-(((1R,2S,3S,6R)-2,3-dihydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 、 乙酸酐 在 吡啶 作用下， 以37%的产率得到(S)-2,2,2-trichloroethyl 4-(((1R,2S,3S,6R)-3-acetoxy-2-hydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin

  摘要：

  The diastereomeric epoxycyclohexenols 3a/b (obtained via a Wharton rearrangement of a bis-epoxycyclohexanone precursor) were shown to undergo interconversion via a facile vinylogous Payne rearrangement. Mechanistic issues were probed; the doubly O-deuterated analogues underwent this equilibration more slowly than the parent dihydroxy compounds. It was possible to kinetically resolve the mixture of 3a/b under equilibrating conditions by use of Amano PS. This DKR is additionally noteworthy because it sets four stereocenters in a single event.

  DOI：

  10.1021/ol902459z