(1R,5R,7E,9R,11S,12S,13E,15S,17S)-17-[tert-butyl(diphenyl)silyl]oxy-9,11-dihydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-4,19-dioxabicyclo[13.3.1]nonadeca-7,13-dien-3-one | 918410-25-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1R,5R,7E,9R,11S,12S,13E,15S,17S)-17-[tert-butyl(diphenyl)silyl]oxy-9,11-dihydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-4,19-dioxabicyclo[13.3.1]nonadeca-7,13-dien-3-one
• CAS: 918410-25-0
• 化学式: C₄₄H₆₆O₇Si
• 分子量: 735.089
• InChiKey: ALCZJXRRXURABT-PLDLPLEVSA-N

物化性质

• 沸点：
  761.4±60.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,5R,7E,9R,11S,12S,13E,15S,17S)-17-[tert-butyl(diphenyl)silyl]oxy-9,11-dihydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-4,19-dioxabicyclo[13.3.1]nonadeca-7,13-dien-3-one 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Total Synthesis of (+)-Acutiphycin

  摘要：

  [GRAPHICS]Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel -catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SMI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.

  DOI：

  10.1021/jo701821h
• 作为产物：
  描述：

  甲醇 、 (5R,7E,9R,11S,12S,13E,15S,17S)-17-[tert-butyl(diphenyl)silyl]oxy-1,9,11-trihydroxy-8,10,10,12,14-pentamethyl-5-pentyl-4,19-dioxabicyclo[13.3.1]nonadeca-7,13-dien-3-one 在 柠檬酸 作用下， 反应 10.0h， 以100%的产率得到(1R,5R,7E,9R,11S,12S,13E,15S,17S)-17-[tert-butyl(diphenyl)silyl]oxy-9,11-dihydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-4,19-dioxabicyclo[13.3.1]nonadeca-7,13-dien-3-one
  参考文献：
  名称：

  Total Synthesis of (+)-Acutiphycin

  摘要：

  [GRAPHICS]Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel -catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SMI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.

  DOI：

  10.1021/jo701821h

文献信息

• Total Synthesis of (+)-Acutiphycin
  作者：Ryan M. Moslin、Timothy F. Jamison

  DOI：10.1021/jo701821h

  日期：2007.12.1

  [GRAPHICS]Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel -catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SMI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.