methyl (2S,3S,5R)-6-(3-bromo-2-hydroxy-5-isopropoxy-6-methoxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate | 1033591-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl (2S,3S,5R)-6-(3-bromo-2-hydroxy-5-isopropoxy-6-methoxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate
• 英文别名: methyl (2S,3S,5R)-6-(3-bromo-2-hydroxy-6-methoxy-5-propan-2-yloxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate
• CAS: 1033591-49-9
• 化学式: C₁₉H₂₉BrO₇
• 分子量: 449.339
• InChiKey: UYFFKEMJUKCBIQ-WHCBVINPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,5R)-6-(3-bromo-2-hydroxy-5-isopropoxy-6-methoxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate 、 2-溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以95%的产率得到methyl (2S,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate
  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,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-3-methoxy-5-methyltetrahydro-2H-pyran-2-carboxylate 在 三乙基硅烷 、 scandium tris(trifluoromethanesulfonate) 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 20.17h， 以72%的产率得到methyl (2S,3S,5R)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-2-hydroxy-3-methoxy-5-methylhexanoate
  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.