(S)-3-((1aR,3aR,3bS,5aS,8aS,8bR,10R,10aR)-10-methoxy-3a,5a-dimethyl-1,1a,2,3,3a,3b,4,5,5a,8,8a,8b,9,10-tetradecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methylbutan-2-ol | 1214260-28-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (S)-3-((1aR,3aR,3bS,5aS,8aS,8bR,10R,10aR)-10-methoxy-3a,5a-dimethyl-1,1a,2,3,3a,3b,4,5,5a,8,8a,8b,9,10-tetradecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methylbutan-2-ol
• CAS: 1214260-28-2
• 化学式: C₂₅H₄₀O₂
• 分子量: 372.591
• InChiKey: VFNUPHZIGYQFRV-SRCRVOQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((1aR,3aR,3bS,5aS,8aS,8bR,10R,10aR)-10-methoxy-3a,5a-dimethyl-1,1a,2,3,3a,3b,4,5,5a,8,8a,8b,9,10-tetradecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methylbutan-2-ol 在 吡啶 、 四氧化锇 作用下， 以 四氢呋喃 、 苯 为溶剂， 以94%的产率得到(1S,2R,5R,7R,8R,10R,11S,13R,14S,15S)-14-[(2R)-3-hydroxy-3-methylbutan-2-yl]-8-methoxy-2,15-dimethylpentacyclo[8.7.0.02,7.05,7.011,15]heptadecane-13,14-diol
  参考文献：
  名称：

  Unusual oxidative transformations of a steroidal 16α,17α,22-triol

  摘要：

  A number of unexpected reactions were observed during attempts to invert configuration at C16 in 16 alpha,17 alpha,22-triol 3a. The PDC oxidation of 3a produced the D-seco-aldehyde 4a. Analogous compound 4b was obtained by Swern oxidation of the 16 alpha,17 alpha-dihydroxy-22-O-TES-ether 3b in addition to the desired 16-ketone 7. The unprotected triol 3a yielded pentacyclic products 5 and 6 under similar conditions. The Mitsunobu reaction of the triol 3a afforded 16-ketone 8 with inverted configuration of the side chain. During heating of a solution of 3a in THF with NaH at reflux autoxidation to the 16-ketone cyclic hemiketal 5, identical to one of the Swern oxidation products, took place. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.10.002
• 作为产物：
  描述：

  甲基碘化镁 、 (20S)-ethyl 6β-methoxy-20-methyl-3α,5-cyclo-5α-pregn-16-en-21-oate 以 四氢呋喃 为溶剂， 生成 (S)-3-((1aR,3aR,3bS,5aS,8aS,8bR,10R,10aR)-10-methoxy-3a,5a-dimethyl-1,1a,2,3,3a,3b,4,5,5a,8,8a,8b,9,10-tetradecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methylbutan-2-ol
  参考文献：
  名称：

  Unusual oxidative transformations of a steroidal 16α,17α,22-triol

  摘要：

  A number of unexpected reactions were observed during attempts to invert configuration at C16 in 16 alpha,17 alpha,22-triol 3a. The PDC oxidation of 3a produced the D-seco-aldehyde 4a. Analogous compound 4b was obtained by Swern oxidation of the 16 alpha,17 alpha-dihydroxy-22-O-TES-ether 3b in addition to the desired 16-ketone 7. The unprotected triol 3a yielded pentacyclic products 5 and 6 under similar conditions. The Mitsunobu reaction of the triol 3a afforded 16-ketone 8 with inverted configuration of the side chain. During heating of a solution of 3a in THF with NaH at reflux autoxidation to the 16-ketone cyclic hemiketal 5, identical to one of the Swern oxidation products, took place. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.10.002