(2S,3S,4R,6S)-6-[(2E,4E,8Z,10E)-(1R,7R)-1-Hydroxy-11-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-5,7,9-trimethyl-undeca-2,4,8,10-tetraenyl]-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-ol | 331686-87-4

• 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: (2S,3S,4R,6S)-6-[(2E,4E,8Z,10E)-(1R,7R)-1-Hydroxy-11-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-5,7,9-trimethyl-undeca-2,4,8,10-tetraenyl]-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-ol
• 英文别名: (2S,3S,4R,6S)-6-[(1R,2E,4E,7R,8Z,10E)-1-hydroxy-5,7,9-trimethyl-11-[(2R,6R)-6-propan-2-yloxy-3,6-dihydro-2H-pyran-2-yl]undeca-2,4,8,10-tetraenyl]-3-methyl-2-[(E)-prop-1-enyl]oxan-4-ol
• CAS: 331686-87-4
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: JMRJDVDNTKCLJA-KFQFURJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,6S)-6-[(2E,4E,8Z,10E)-(1R,7R)-1-Hydroxy-11-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-5,7,9-trimethyl-undeca-2,4,8,10-tetraenyl]-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-ol 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 丙酮 为溶剂， 以83%的产率得到(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
• 作为产物：
  描述：

  1-甲氧基-1,3-丁二烯 在 palladium diacetate titanium(IV) isopropylate 、 lithium aluminium tetrahydride 、 草酰氯 、 potassium tert-butylate 、 四丁基溴化铵 、 (R)-1,1'-Bi-2-naphthol 、 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 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.33h， 生成 (2S,3S,4R,6S)-6-[(2E,4E,8Z,10E)-(1R,7R)-1-Hydroxy-11-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-5,7,9-trimethyl-undeca-2,4,8,10-tetraenyl]-3-methyl-2-((E)-propenyl)-tetrahydro-pyran-4-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.