(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile | 1053726-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile
• 英文别名: (Z,8R)-8-[tert-butyl(diphenyl)silyl]oxy-8-[(2S,4S,5S)-4-[tert-butyl(diphenyl)silyl]oxy-5-[(E)-3-oxooct-1-enyl]oxolan-2-yl]oct-5-enenitrile
• CAS: 1053726-54-7
• 化学式: C₅₂H₆₇NO₄Si₂
• 分子量: 826.279
• InChiKey: MCBIDBXIVYLDAU-XDUCYJIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.38
• 重原子数：
  59
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile 在 sodium hydroxide 、 四丁基氟化铵 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.25h， 生成 (Z)-(R)-8-Hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-((E)-(R)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid
  参考文献：
  名称：

  A Flexible Enantioselective Synthesis of the Isofurans

  摘要：

  Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products, the isofurans (IsoF's), was reported. These new compounds are available from natural sources only in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide intermediate and its conversion to the enantiomerically pure isofurans SC-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.

  DOI：

  10.1021/jo048863o
• 作为产物：
  描述：

  (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以93%的产率得到(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile
  参考文献：
  名称：

  A Flexible Enantioselective Synthesis of the Isofurans

  摘要：

  Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products, the isofurans (IsoF's), was reported. These new compounds are available from natural sources only in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide intermediate and its conversion to the enantiomerically pure isofurans SC-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.

  DOI：

  10.1021/jo048863o

文献信息

• A Flexible Enantioselective Synthesis of the Isofurans
  作者：Douglass F. Taber、Yongchun Pan、Xia Zhao

  DOI：10.1021/jo048863o

  日期：2004.10.1

  Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products, the isofurans (IsoF's), was reported. These new compounds are available from natural sources only in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide intermediate and its conversion to the enantiomerically pure isofurans SC-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.