Acetic acid (E)-(S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aS,6S,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-but-2-enyl ester | 908145-99-3

• 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: Acetic acid (E)-(S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aS,6S,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-but-2-enyl ester
• 英文别名: [(E,1S)-4-[(2S,4aS,6R,8aS)-2-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-4a-methyl-3,4,6,7,8,8a-hexahydro-2H-pyrano[3,2-b]pyran-6-yl]-1-[(2R,5R)-5-(2-acetyloxypropan-2-yl)-2-methyloxolan-2-yl]-4-oxobut-2-enyl] acetate
• CAS: 908145-99-3
• 化学式: C₃₃H₅₁BrO₉
• 分子量: 671.667
• InChiKey: XDKXCRSABXZYOA-DTPAXSHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (E)-(S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aS,6S,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-but-2-enyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以90%的产率得到Acetic acid (S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aS,6S,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-butyl ester
  参考文献：
  名称：

  7,11-epi-Thyrsiferol:  Completion of Its Synthesis, Evaluation of Its Antimitotic Properties, and the Further Development of an SAR Model

  摘要：

  We (a) describe the completion of a total synthesis of 7,11-epi-thyrsiferol (4), (b) compare the antimitotic activities of thyrsiferol (2), Delta(15,28)-dehydrothyrsiferol (3), and 7,11-epi-thyrsiferol (4), (c) evaluate the synergistic behavior of the title compound and colchicine to inhibit cell proliferation, and (d) describe the results of conformational searches that provide additional insight concerning the SAR profile of the thyrsiferol family of natural products.

  DOI：

  10.1021/jo060519z
• 作为产物：
  描述：

  Acetic acid (E)-(S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aS,6S,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-hydroxy-but-2-enyl ester 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到Acetic acid (E)-(S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aS,6S,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-but-2-enyl ester
  参考文献：
  名称：

  7,11-epi-Thyrsiferol:  Completion of Its Synthesis, Evaluation of Its Antimitotic Properties, and the Further Development of an SAR Model

  摘要：

  We (a) describe the completion of a total synthesis of 7,11-epi-thyrsiferol (4), (b) compare the antimitotic activities of thyrsiferol (2), Delta(15,28)-dehydrothyrsiferol (3), and 7,11-epi-thyrsiferol (4), (c) evaluate the synergistic behavior of the title compound and colchicine to inhibit cell proliferation, and (d) describe the results of conformational searches that provide additional insight concerning the SAR profile of the thyrsiferol family of natural products.

  DOI：

  10.1021/jo060519z