(4S,2'R,3'S,4'S,5'S)-4-benzyl-3-(2',5'-diphenethyl-4'-vinyltetrahydrofuran-3'-carbonyl)-oxazolidin-2-one | 868696-82-6

• 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,2'R,3'S,4'S,5'S)-4-benzyl-3-(2',5'-diphenethyl-4'-vinyltetrahydrofuran-3'-carbonyl)-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2R,3S,4S,5S)-4-ethenyl-2,5-bis(2-phenylethyl)oxolane-3-carbonyl]-1,3-oxazolidin-2-one
• CAS: 868696-82-6
• 化学式: C₃₃H₃₅NO₄
• 分子量: 509.645
• InChiKey: QNIPRQNNQXXPJQ-LIIQBVBMSA-N

物化性质

• 沸点：
  680.1±55.0 °C(predicted)
• 密度：
  1.184±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,2'R,3'S,4'S,5'S)-4-benzyl-3-(2',5'-diphenethyl-4'-vinyltetrahydrofuran-3'-carbonyl)-oxazolidin-2-one 在 sodium tetrahydroborate 、 Grubbs catalyst first generation 、 正丁基锂 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,3R,3aS,6aR)-1,3-Diphenethyl-1,3,3a,6a-tetrahydro-cyclopenta[c]furan-4-one
  参考文献：
  名称：

  Stereoselective synthesis of the octahydroisobenzofuran skeleton of the eunicellins

  摘要：

  A de novo asymmetric synthesis of the octahydroisobenzofuran skeleton contained within the eunicellin family of natural products has been completed. The key transformations involve the convergent assembly of a tetrasubstituted tetrahydrofuran by condensation of a functionalised allylsiloxane with an aldehyde; controlled epimerisation of a C4 aldehyde by intramolecular trapping; installation of the isopropyl substituent by stereoselective Michael addition to a 5,5-bicyclic enone; and ring expansion of the 5,5-system to the target structure by radical-mediated cyclopropane fragmentation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.046
• 作为产物：
  描述：

  (4S,6'S,7'R)-4-benzyl-3-(2',2'-dimethyl-7'-phenethyl-2',3',6',7'-tetrahydro-[1',2']oxasilepine-6'-carbonyl)oxazolidin-2-one 、 苯丙醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 以91%的产率得到(4S,2'R,3'S,4'S,5'S)-4-benzyl-3-(2',5'-diphenethyl-4'-vinyltetrahydrofuran-3'-carbonyl)-oxazolidin-2-one
  参考文献：
  名称：

  四取代四氢呋喃的立体控制组装：virgatusin的简明合成。

  摘要：

  取代的烯丙基硅氧烷与醛的缩合导致2,3,4,5-四取代的四氢呋喃的高度立体选择性结构。与富电子的芳基和α，β-不饱和醛作为底物，在C5中的立体化学结果可以通过路易斯酸适当地选择决定。该反应已用于（+）-维他汀（ent-1）的简明（九步）合成。[反应：看文字]

  DOI：

  10.1021/ol051292h

文献信息

• Stereoselective synthesis of the octahydroisobenzofuran skeleton of the eunicellins
  作者：Tito Akindele、Stephen P. Marsden、John G. Cumming

  DOI：10.1016/j.tetlet.2005.08.046

  日期：2005.10

  A de novo asymmetric synthesis of the octahydroisobenzofuran skeleton contained within the eunicellin family of natural products has been completed. The key transformations involve the convergent assembly of a tetrasubstituted tetrahydrofuran by condensation of a functionalised allylsiloxane with an aldehyde; controlled epimerisation of a C4 aldehyde by intramolecular trapping; installation of the isopropyl substituent by stereoselective Michael addition to a 5,5-bicyclic enone; and ring expansion of the 5,5-system to the target structure by radical-mediated cyclopropane fragmentation. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereocontrolled Assembly of Tetrasubstituted Tetrahydrofurans:  A Concise Synthesis of Virgatusin
  作者：Tito Akindele、Stephen P. Marsden、John G. Cumming

  DOI：10.1021/ol051292h

  日期：2005.8.1

  The condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and alpha,beta-unsaturated aldehydes as substrates, the stereochemical outcome at C5 can be dictated by appropriate choice of Lewis acid. The reaction has been applied to a concise (nine step) synthesis of (+)-virgatusin (ent-1)

  取代的烯丙基硅氧烷与醛的缩合导致2,3,4,5-四取代的四氢呋喃的高度立体选择性结构。与富电子的芳基和α，β-不饱和醛作为底物，在C5中的立体化学结果可以通过路易斯酸适当地选择决定。该反应已用于（+）-维他汀（ent-1）的简明（九步）合成。[反应：看文字]