[(2R,4R,6R)-2-methoxy-6-[(3S)-3-methylpent-4-enyl]-2-[(4R)-2-oxo-1,3-thiazolidin-4-yl]oxan-4-yl] (2Z)-3-methylhepta-2,6-dienoate | 1114568-08-9

• 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: [(2R,4R,6R)-2-methoxy-6-[(3S)-3-methylpent-4-enyl]-2-[(4R)-2-oxo-1,3-thiazolidin-4-yl]oxan-4-yl] (2Z)-3-methylhepta-2,6-dienoate
• CAS: 1114568-08-9
• 化学式: C₂₃H₃₅NO₅S
• 分子量: 437.601
• InChiKey: CBEFTYHZMGEFJK-AIIXKSJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,4R,6R)-2-methoxy-6-[(3S)-3-methylpent-4-enyl]-2-[(4R)-2-oxo-1,3-thiazolidin-4-yl]oxan-4-yl] (2Z)-3-methylhepta-2,6-dienoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 6,7-(E)-15-OMe-Latrunculin B 、 6,7-(Z)-15-OMe-Latrunculin B
  参考文献：
  名称：

  Examination of the olefin–olefin ring closing metathesis to prepare Latrunculin B

  摘要：

  Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle, Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products. (C 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.144
• 作为产物：
  描述：

  甲醇 、 [(2R,4R,6R)-2-hydroxy-6-[(3S)-3-methylpent-4-enyl]-2-[(4R)-2-oxo-1,3-thiazolidin-4-yl]oxan-4-yl] (2Z)-3-methylhepta-2,6-dienoate 在 对甲苯磺酸 作用下， 反应 20.0h， 以91%的产率得到[(2R,4R,6R)-2-methoxy-6-[(3S)-3-methylpent-4-enyl]-2-[(4R)-2-oxo-1,3-thiazolidin-4-yl]oxan-4-yl] (2Z)-3-methylhepta-2,6-dienoate
  参考文献：
  名称：

  Examination of the olefin–olefin ring closing metathesis to prepare Latrunculin B

  摘要：

  Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle, Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products. (C 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.144

文献信息

• Examination of the olefin–olefin ring closing metathesis to prepare Latrunculin B
  作者：Jin She、John W. Lampe、Alexandra B. Polianski、Paul S. Watson

  DOI：10.1016/j.tetlet.2008.10.144

  日期：2009.1

  Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle, Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products. (C 2008 Elsevier Ltd. All rights reserved.