3β,20R-bis(acetoxy)-5α-12α-hydroxy-pregn-14-ene | 1360763-45-6

• 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: 3β,20R-bis(acetoxy)-5α-12α-hydroxy-pregn-14-ene
• CAS: 1360763-45-6
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: TYYWPBJMYYRWSX-DJGVDCCISA-N

反应信息

• 作为产物：
  描述：

  在 水 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以61 mg的产率得到3β,20R-bis(acetoxy)-5α-12α-14β-dihydroxy-pregnane
  参考文献：
  名称：

  Norrish–Prins reaction as a key step in the synthesis of 14β-hydroxy-5α (or 5β or Δ5,6)-pregnane derivatives

  摘要：

  Numerous bioactive glycosteroids are characterized by aglycones bearing a 14 beta-hydroxy pregnane skeleton like boucerin and isoramanone. In general, the syntheses of the latter are achieved by acidic hydrolysis of the corresponding glycosteroids. These aglycones were also obtained by a combined Norrish type I-Prins reaction starting from the corresponding 12-keto-pregnane derivatives. However, for the Norrish-Prins reaction, no reports describe the influence of the A/B ring junction (cis or trans or Delta(5,6) double bond) or the influence of the substitution pattern at position 20. Herein, we describe the use of Norrish type I-Prins reactions to synthesize isoramanone and boucerin derivatives and their A/B cis and trans analogs. The influence of the parameters mentioned above is also presented. These studies showed that the A/B ring junction has little influence on the Norrish type I-Prins reaction but that the substitution pattern at position 20 is important. The presence of a dioxolane group induced not only the formation of the desired 14 beta-hydroxy pregnane derivatives in the highest yields but also the formation of new spiro derivatives. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.004