methyl (2S,3S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-3-[(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy]tetrahydro-2H-pyran-2-carboxylate | 1033591-61-5

• 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,3S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-3-[(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy]tetrahydro-2H-pyran-2-carboxylate
• CAS: 1033591-61-5
• 化学式: C₃₁H₃₈BrF₃O₉
• 分子量: 691.537
• InChiKey: ZDYACFDCTNQLFB-SLYLEEKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  methyl (2S,3S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-carboxylate 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以64.3%的产率得到methyl (2S,3S,5S,6S)-6-(3-bromo-2,5-diisopropoxy-6-methoxyphenyl)-5-methyl-3-[(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy]tetrahydro-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