methyl (2S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate | 1033591-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (2S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate
• 英文别名: methyl (2S,3S,6S)-2-[5-bromo-2-methoxy-3,6-di(propan-2-yloxy)phenyl]-3-methyl-3,6-dihydro-2H-pyran-6-carboxylate
• CAS: 1033591-47-7
• 化学式: C₂₁H₂₉BrO₆
• 分子量: 457.362
• InChiKey: RTZRMESYEDMXNR-YEWWUXTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-bromo-2,5-diisopropoxy-6-methoxybenzaldehyde 、 methyl (2R,3S)-(E)-3-(dimethyl(phenyl)silyl)-2-(trimethylsilyloxy)-hex-4-enoate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl (2S,5S,6R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate 、 methyl (2S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate
  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.