(Z)-methyl 4-((2S,4S,6S)-6-(((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)but-2-enoate | 1222190-42-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-methyl 4-((2S,4S,6S)-6-(((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)but-2-enoate
• 英文别名: methyl (Z)-4-[(2S,4S,6S)-6-[[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl]-2-phenyl-1,3-dioxan-4-yl]but-2-enoate
• CAS: 1222190-42-2
• 化学式: C₃₃H₄₄O₆
• 分子量: 536.709
• InChiKey: PDECBPVFSJXQFU-QLULXTCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 4-((2S,4S,6S)-6-(((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)but-2-enoate 在 溶剂黄146 作用下， 反应 18.0h， 以82%的产率得到(+)-polyrhacitide A
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-polyrhacitide A

  摘要：

  A facile stereoselective total synthesis of secondary metabolite (+)-polyrhacitide A is described. Stereoselective aldol reaction, Horner-Wardsworth-Emmons reaction, Evans acetal intramolecular oxa-Michael reaction and diastereoselective syn reduction reaction are the key steps involved in the target synthesis. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.070
• 作为产物：
  描述：

  2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde 、 O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以90%的产率得到(Z)-methyl 4-((2S,4S,6S)-6-(((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)but-2-enoate
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-polyrhacitide A

  摘要：

  A facile stereoselective total synthesis of secondary metabolite (+)-polyrhacitide A is described. Stereoselective aldol reaction, Horner-Wardsworth-Emmons reaction, Evans acetal intramolecular oxa-Michael reaction and diastereoselective syn reduction reaction are the key steps involved in the target synthesis. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.070

文献信息

• Stereoselective total synthesis of (+)-polyrhacitide A
  作者：J.S. Yadav、G. Rajendar、B. Ganganna、P. Srihari

  DOI：10.1016/j.tetlet.2010.02.070

  日期：2010.4

  A facile stereoselective total synthesis of secondary metabolite (+)-polyrhacitide A is described. Stereoselective aldol reaction, Horner-Wardsworth-Emmons reaction, Evans acetal intramolecular oxa-Michael reaction and diastereoselective syn reduction reaction are the key steps involved in the target synthesis. (c) 2010 Elsevier Ltd. All rights reserved.