methyl (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-enoate | 1033591-56-8

• 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: methyl (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-enoate
• 英文别名: methyl (E,2S,5S,6R,7S,9R)-10-[5-bromo-2-methoxy-3,6-di(propan-2-yloxy)phenyl]-7-methoxy-2-(methoxymethoxy)-3,5,9-trimethyl-6-phenylmethoxydec-3-enoate
• CAS: 1033591-56-8
• 化学式: C₃₇H₅₅BrO₉
• 分子量: 723.742
• InChiKey: WSPNKDIHUVZAFJ-SPRIETJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (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-enoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 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：

  methyl (2R,3R,E)-3-(dimethyl(phenyl)silyl)-2-(methoxymethoxy)-3-methylhex-4-enoate 、 (2S,4R)-5-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-2-methoxy-4-methylpentanal 、 苄氧基三甲基硅烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 73.0h， 以70%的产率得到methyl (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-enoate
  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.