(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6,12-dimethoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid | 1033591-58-0

• 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: (2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6,12-dimethoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid
• 英文别名: (2E,4Z,6S,7S,8E,10S,11R,12S,14R)-15-[5-bromo-2-methoxy-3,6-di(propan-2-yloxy)phenyl]-6,12-dimethoxy-7-(methoxymethoxy)-2,8,10,14-tetramethyl-11-phenylmethoxypentadeca-2,4,8-trienoic acid
• CAS: 1033591-58-0
• 化学式: C₄₃H₆₃BrO₁₀
• 分子量: 819.871
• InChiKey: YEWGXZANQUCSTE-AACQPJEMSA-N

物化性质

• 沸点：
  806.7±65.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  54
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6,12-dimethoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid 、 氯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成
  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
• 作为产物：
  描述：

  (2E,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6,12-dimethoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dien-4-ynoic acid 在 吡啶 、 Lindlar's catalyst 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.83h， 以90%的产率得到(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-15-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-6,12-dimethoxy-7-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid
  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.