(2R,6R)-2-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-6-isopropoxy-3,6-dihydro-2H-pyran | 321995-01-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,6R)-2-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-6-isopropoxy-3,6-dihydro-2H-pyran
• 英文别名: tert-butyl-[(1R,2E,4E,7R,8Z,10E)-1-[(2S,4R,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyl-6-[(E)-prop-1-enyl]oxan-2-yl]-5,7,9-trimethyl-11-[(2R,6R)-6-propan-2-yloxy-3,6-dihydro-2H-pyran-2-yl]undeca-2,4,8,10-tetraenoxy]-dimethylsilane
• CAS: 321995-01-1
• 化学式: C₄₃H₇₆O₅Si₂
• 分子量: 729.244
• InChiKey: OGGVENWETXEWFR-GWFFGOBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.26
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,6R)-2-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-6-isopropoxy-3,6-dihydro-2H-pyran 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以100%的产率得到(2R,6R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-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 63.33h， 生成 (2R,6R)-2-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-6-isopropoxy-3,6-dihydro-2H-pyran
  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

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

  DOI：10.1002/1521-3773(20001201)39:23<4364::aid-anie4364>3.0.co;2-g

  日期：2000.12.1
• 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.