(2E,4E,7S,8R,9S,10R,11S)-12-(tert-butyldimethylsilyloxy)-8-hydroxy-10-methoxy-1-(4-methoxybenzyloxy)-3,5,7,9,11-pentamethyldodeca-2,4-dien-6-one | 1187629-77-1

• 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: (2E,4E,7S,8R,9S,10R,11S)-12-(tert-butyldimethylsilyloxy)-8-hydroxy-10-methoxy-1-(4-methoxybenzyloxy)-3,5,7,9,11-pentamethyldodeca-2,4-dien-6-one
• CAS: 1187629-77-1
• 化学式: C₃₂H₅₄O₆Si
• 分子量: 562.863
• InChiKey: UYFGNZFQBDBCHZ-WNFJJOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  39.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2E,4E,7S,8R,9S,10R,11S)-12-(tert-butyldimethylsilyloxy)-8-hydroxy-10-methoxy-1-(4-methoxybenzyloxy)-3,5,7,9,11-pentamethyldodeca-2,4-dien-6-one 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以97%的产率得到(2S,3R,4S,5S,6S,7R,8E,10E)-1-(tert-butyldimethylsilyloxy)-3-methoxy-12-(4-methoxybenzyloxy)-2,4,6,8,10-pentamethyldodeca-8,10-diene-5,7-diol
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833
• 作为产物：
  描述：

  (2E,4E,7S,8R,9R,10R,11S)-12-(tert-butyldimethylsilyloxy)-10-methoxy-1-(4-methoxybenzyloxy)-3,5,7,9,11-pentamethyl-8-(trimethylsilyloxy)dodeca-2,4-dien-6-one 在 amberlyst-15 作用下， 以 甲醇 为溶剂， 以51%的产率得到(2E,4E,7S,8R,9S,10R,11S)-12-(tert-butyldimethylsilyloxy)-8-hydroxy-10-methoxy-1-(4-methoxybenzyloxy)-3,5,7,9,11-pentamethyldodeca-2,4-dien-6-one
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833