(E)-(4R,5R,6S,7S,8R,9R,10R)-11-Benzyloxy-5,7,9-trihydroxy-4,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester | 177929-78-1

• 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: (E)-(4R,5R,6S,7S,8R,9R,10R)-11-Benzyloxy-5,7,9-trihydroxy-4,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4R,5R,6S,7S,8R,9R,10R)-5,7,9-trihydroxy-4,6,8,10-tetramethyl-11-phenylmethoxyundec-2-enoate
• CAS: 177929-78-1
• 化学式: C₂₄H₃₈O₆
• 分子量: 422.562
• InChiKey: PNBWPRJFTMSCQO-UURINDJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5R,6S,7S,8R,9R,10R)-11-Benzyloxy-5,7,9-trihydroxy-4,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 水 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (E)-(4S,5S,6R,7R,8S,9R,10R,11R,12R)-13-Benzyloxy-5,7,9,11-tetrahydroxy-2,4,6,8,10,12-hexamethyl-tridec-2-enoic acid ethyl ester
  参考文献：
  名称：

  Tandem synthesis of polypropionate chains–highly stereoselective synthesis of the ansa chain of streptovaricin U and protostreptovaricins based on stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium

  摘要：

  The highly stereoselective synthesis of the ansa chain segment 23 of streptovaricin U and protostreptovaricins (I and II) is achieved by stereospecific methylation of gamma,delta-epoxy acrylates with trimethylaluminium.

  DOI：

  10.1039/cc9960001027
• 作为产物：
  描述：

  (E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (E)-(4R,5R,6S,7S,8R,9R,10R)-11-Benzyloxy-5,7,9-trihydroxy-4,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester
  参考文献：
  名称：

  Tandem synthesis of polypropionate chains–highly stereoselective synthesis of the ansa chain of streptovaricin U and protostreptovaricins based on stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium

  摘要：

  The highly stereoselective synthesis of the ansa chain segment 23 of streptovaricin U and protostreptovaricins (I and II) is achieved by stereospecific methylation of gamma,delta-epoxy acrylates with trimethylaluminium.

  DOI：

  10.1039/cc9960001027

文献信息

• Tandem synthesis of polypropionate chains–highly stereoselective synthesis of the ansa chain of streptovaricin U and protostreptovaricins based on stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium
  作者：Masaaki Miyashita、Tomonori Shiratani、Katsumi Kawamine、Susumi Hatakeyama、Hiroshi Irie

  DOI：10.1039/cc9960001027

  日期：——

  The highly stereoselective synthesis of the ansa chain segment 23 of streptovaricin U and protostreptovaricins (I and II) is achieved by stereospecific methylation of gamma,delta-epoxy acrylates with trimethylaluminium.