2-[(1R,2R,4R,5S,6S,9S,10R,13R)-6-[(2R)-3-hydroxy-2,3-dimethylbutanoyl]-2-methoxy-6,10-dimethyl-5-tetracyclo[8.4.0.01,13.04,9]tetradecanyl]acetaldehyde | 1214260-30-6

• 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: 2-[(1R,2R,4R,5S,6S,9S,10R,13R)-6-[(2R)-3-hydroxy-2,3-dimethylbutanoyl]-2-methoxy-6,10-dimethyl-5-tetracyclo[8.4.0.01,13.04,9]tetradecanyl]acetaldehyde
• CAS: 1214260-30-6
• 化学式: C₂₅H₄₀O₄
• 分子量: 404.59
• InChiKey: NUFVWSAXAIZKBT-KOBLDJOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (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 在 重铬酸吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以85%的产率得到2-[(1R,2R,4R,5S,6S,9S,10R,13R)-6-[(2R)-3-hydroxy-2,3-dimethylbutanoyl]-2-methoxy-6,10-dimethyl-5-tetracyclo[8.4.0.01,13.04,9]tetradecanyl]acetaldehyde
  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

文献信息

• Unusual oxidative transformations of a steroidal 16α,17α,22-triol
  作者：Jacek W. Morzycki、José Oscar H. Pérez-Díaz、Rosa Santillan、Agnieszka Wojtkielewicz

  DOI：10.1016/j.steroids.2009.10.002

  日期：2010.1

  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.