(S)-2,2,2-trichloroethyl 4-(((1S,2R,3R,6S)-2,3-dihydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 1202810-28-3

• 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-(((1S,2R,3R,6S)-2,3-dihydroxy-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-[[(1S,2R,3R,6S)-2,3-dihydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1202810-28-3
• 化学式: C₁₅H₂₀Cl₃NO₆
• 分子量: 416.686
• InChiKey: IKKOEJPBSKFCBN-GRZGAGJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2,2,2-trichloroethyl 4-(((1S,2R,3R,6S)-2,3-dihydroxy-7-oxabicyclo[4.1.0]hept-4-en-2-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以39%的产率得到(S)-2,2,2-trichloroethyl 4-(((1S,2S,6S)-2-hydroxy-3-oxo-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
• 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 以 氘代氯仿 为溶剂， 反应 72.0h， 生成 (S)-2,2,2-trichloroethyl 4-(((1S,2R,3R,6S)-2,3-dihydroxy-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

文献信息

• Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin
  作者：Thomas R. Hoye、Christopher S. Jeffrey、Dorian P. Nelson

  DOI：10.1021/ol902459z

  日期：2010.1.1

  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.