(1R,2S,4S,7S,8S,9S,12S,13R,16R,18R,19R)-19-methoxy-6,6,7,9,13-pentamethyl-5-oxahexacyclo[10.8.0.02,9.04,8.013,18.016,18]icosan-8-ol | 1214260-32-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,4S,7S,8S,9S,12S,13R,16R,18R,19R)-19-methoxy-6,6,7,9,13-pentamethyl-5-oxahexacyclo[10.8.0.02,9.04,8.013,18.016,18]icosan-8-ol
• CAS: 1214260-32-8
• 化学式: C₂₅H₄₀O₃
• 分子量: 388.591
• InChiKey: UFGORBBGZNBUIZ-QZQQHLATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

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 草酸氯化物 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.28h， 以45%的产率得到(1R,2S,4S,7S,8S,9S,12S,13R,16R,18R,19R)-19-methoxy-6,6,7,9,13-pentamethyl-5-oxahexacyclo[10.8.0.02,9.04,8.013,18.016,18]icosane-4,8-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