(2R,6R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-Hydroxy-11-[(2S,4R,5S,6S)-4-hydroxy-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-2H-pyran-2-ol | 331686-88-5

• 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,6R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-Hydroxy-11-[(2S,4R,5S,6S)-4-hydroxy-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-2H-pyran-2-ol
• 英文别名: (2S,3S,4R,6S)-6-[(1R,2E,4E,7R,8Z,10E)-1-hydroxy-11-[(2R,6R)-6-hydroxy-3,6-dihydro-2H-pyran-2-yl]-5,7,9-trimethylundeca-2,4,8,10-tetraenyl]-3-methyl-2-[(E)-prop-1-enyl]oxan-4-ol
• CAS: 331686-88-5
• 化学式: C₂₈H₄₂O₅
• 分子量: 458.638
• InChiKey: CNKYQAYJFGEPTQ-DPBKJIEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,6R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-Hydroxy-11-[(2S,4R,5S,6S)-4-hydroxy-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-2H-pyran-2-ol 以20%的产率得到(+)-ratjadone
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g
• 作为产物：
  描述：

  cis-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran 在 palladium diacetate 草酰氯 、 potassium tert-butylate 、 四丁基溴化铵 、 4-甲基苯磺酸吡啶 、 caesium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 27.08h， 生成 (2R,6R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-Hydroxy-11-[(2S,4R,5S,6S)-4-hydroxy-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-2H-pyran-2-ol
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g

文献信息

• The First Total Synthesis of (+)-Ratjadone
  作者：Ulhas Bhatt、Mathias Christmann、Monika Quitschalle、Eckhard Claus、Markus Kalesse

  DOI：10.1021/jo005768g

  日期：2001.3.1

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.