(2R,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol | 1033591-55-7

• 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: (2R,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol
• CAS: 1033591-55-7
• 化学式: C₂₁H₃₅BrO₆
• 分子量: 463.409
• InChiKey: AUXYOKTYTBJODG-OLMNPRSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol 在 sodium periodate 、 水 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 0.83h， 以96%的产率得到(2S,4R)-5-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-2-methoxy-4-methylpentanal
  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 (2S,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate 在 甲醇 、 锂硼氢 、 盐酸 、 水 作用下， 以 乙醚 为溶剂， 反应 6.33h， 以98%的产率得到(2R,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol
  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