(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-(benzyloxy)-9-hydroxy-12,15-diisopropoxy-14,8,14-trimethoxy-4,10,12,16-tetramethyl-2-aza-1(1,3)-benzenacycloheptadecaphane-4,6,10-trien-3-one | 1033591-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-(benzyloxy)-9-hydroxy-12,15-diisopropoxy-14,8,14-trimethoxy-4,10,12,16-tetramethyl-2-aza-1(1,3)-benzenacycloheptadecaphane-4,6,10-trien-3-one
• CAS: 1033591-60-4
• 化学式: C₄₁H₅₉NO₈
• 分子量: 693.921
• InChiKey: WGXWXFOYSBGENZ-BSSVYLHFSA-N

物化性质

• 沸点：
  803.1±65.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  104.71
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-(benzyloxy)-9-hydroxy-12,15-diisopropoxy-14,8,14-trimethoxy-4,10,12,16-tetramethyl-2-aza-1(1,3)-benzenacycloheptadecaphane-4,6,10-trien-3-one 、 三氯乙酰异氰酸酯 以 二氯甲烷 为溶剂， 反应 0.5h， 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,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-trienelactame 在 甲醇 、 乙酰氯 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以91%的产率得到(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-(benzyloxy)-9-hydroxy-12,15-diisopropoxy-14,8,14-trimethoxy-4,10,12,16-tetramethyl-2-aza-1(1,3)-benzenacycloheptadecaphane-4,6,10-trien-3-one
  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