ethyl (2E,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6-hydroxy-12-methoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dien-4-ynoate | 1033591-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (2E,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6-hydroxy-12-methoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dien-4-ynoate
• 英文别名: ethyl (2E,6S,7S,8E,10S,11R,12S,14R)-15-[5-bromo-2-methoxy-3,6-di(propan-2-yloxy)phenyl]-6-hydroxy-12-methoxy-7-(methoxymethoxy)-2,8,10,14-tetramethyl-11-phenylmethoxypentadeca-2,8-dien-4-ynoate
• CAS: 1033591-51-3
• 化学式: C₄₄H₆₃BrO₁₀
• 分子量: 831.882
• InChiKey: RGUDXBDNPRMUPO-TVBKHCAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  55
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2S,5S,6R,7S,9R,E)-6-(benzyloxy)-10-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-7-methoxy-2-(methoxymethoxy)-3,5,9-trimethyldec-3-enal 、 ethyl (E)-2-methyl-2-penten-4-ynoate 在 正丁基锂 、 zinc(II) chloride 、 氯化铵 作用下， 以 乙醚 、 正庚烷 、 正己烷 、 水 为溶剂， 反应 0.67h， 以76%的产率得到ethyl (2E,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6-hydroxy-12-methoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dien-4-ynoate
  参考文献：
  名称：

  Total Synthesis of the Hsp90 Inhibitor Geldanamycin

  摘要：

  An enantioselective synthesis of the Hsp90 inhibitor geldanamycin was achieved in 20 linear steps and 2.0% overall yield from 2-methoxyhydroquinone. The synthesis is highlighted by a regio- and stereoselective hydroboration reaction; a Sc(OTf)(3)/Et(3)SiH-mediated pyran ring-opening reaction; an enantioselective crotylation to simultaneously install the C8-C9 (E)-trisubstituted olefin, the C10 and C11 stereocenters; a chelation-controlled asymmetric metallated acetylide addition; and an intramolecular copper(I)-mediated aryl amidation reaction to close the 19-membered macrolactam.

  DOI：

  10.1021/ol800749w

文献信息

• Total Synthesis of the Hsp90 Inhibitor Geldanamycin
  作者：Hua-Li Qin、James S. Panek

  DOI：10.1021/ol800749w

  日期：2008.6.1

  An enantioselective synthesis of the Hsp90 inhibitor geldanamycin was achieved in 20 linear steps and 2.0% overall yield from 2-methoxyhydroquinone. The synthesis is highlighted by a regio- and stereoselective hydroboration reaction; a Sc(OTf)(3)/Et(3)SiH-mediated pyran ring-opening reaction; an enantioselective crotylation to simultaneously install the C8-C9 (E)-trisubstituted olefin, the C10 and C11 stereocenters; a chelation-controlled asymmetric metallated acetylide addition; and an intramolecular copper(I)-mediated aryl amidation reaction to close the 19-membered macrolactam.