ethyl (E,4R,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxyhex-2-enoate | 1192356-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (E,4R,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxyhex-2-enoate
• CAS: 1192356-70-9
• 化学式: C₂₀H₂₉NO₆
• 分子量: 379.453
• InChiKey: SDUWEWIWXVQYNC-PUENXVRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (E,4R,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxyhex-2-enoate 在 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 、 mineral oil 、 水 为溶剂， 以0.375 g的产率得到ethyl 2-[(2R,3S,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxyoxolan-2-yl]acetate
  参考文献：
  名称：

  Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach

  摘要：

  2-epi-Jaspine B has been synthesized starting from (-)-diethyl tartrate in 12 simple steps and 26.6% overall yield. The key intermediate was obtained via stereoselective base-catalyzed intramolecular oxy-Michael conjugate addition followed by tandem hydrogenation/hydrogenolysis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.004
• 作为产物：
  描述：

  tert-butyl (4S)-4-[(1R,2E)-1-(benzyloxy)-4-ethoxy-4-oxo-2-butenyl]-2,2-dimethyl-1,3-oxazolane-3-carboxylate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 ethyl (E,4R,5S)-6-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylmethoxyhex-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach

  摘要：

  2-epi-Jaspine B has been synthesized starting from (-)-diethyl tartrate in 12 simple steps and 26.6% overall yield. The key intermediate was obtained via stereoselective base-catalyzed intramolecular oxy-Michael conjugate addition followed by tandem hydrogenation/hydrogenolysis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.004

文献信息

• Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach
  作者：Gowrisankar Reddipalli、Mallam Venkataiah、Mithilesh Kumar Mishra、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2009.07.004

  日期：2009.8

  2-epi-Jaspine B has been synthesized starting from (-)-diethyl tartrate in 12 simple steps and 26.6% overall yield. The key intermediate was obtained via stereoselective base-catalyzed intramolecular oxy-Michael conjugate addition followed by tandem hydrogenation/hydrogenolysis. (c) 2009 Elsevier Ltd. All rights reserved.