5-pregnen-3β,15β,17α,20(S)-tetrol | 37126-75-3

• 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: 5-pregnen-3β,15β,17α,20(S)-tetrol
• 英文别名: 5-pregnene-3β,15β,17α,20α-tetrol；5-pregnene-3β,15β,17α,20(S)-tetrol；(3S,8R,9S,10R,13S,14S,15R,17R)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,15,17-triol
• CAS: 37126-75-3
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: CVIFELSOWXSKGA-HKTHEYJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  15β,17α,21-trihydroxy-4-pregnen-3,20-dione 在 sodium tetrahydroborate 、 高氯酸 、 sodium iodide 、 锌 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 7.1h， 生成 5-pregnen-3β,15β,17α,20(S)-tetrol
  参考文献：
  名称：

  15β-hydroxysteroids (Part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20-one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione

  摘要：

  A simple three-step synthetic method is reported on the conversion of Delta(4)-3-ketosteroids to the corresponding 3 beta-hydroxy-Delta(5)-steroid analogues. 17 alpha-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3 beta, 17 alpha-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17 alpha-diacetoxy-3,5-pregnadien-20-one(14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione (8), product of Penicillium citrinum fermentation, to the desired 3 beta,15 beta 17 alpha-trihydroxy-5-pregen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3, 15 beta,17 alpha-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydride gave 5-pregnen-3 beta,15 beta,17 alpha,20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with methanolic sodium hydroxide the desired product 3 beta, 15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1) in good yield (54%).

  DOI：

  10.1016/0039-128x(95)00170-u

文献信息

• 15β-hydroxysteroids (Part III). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20-one. Application of n-butyl boronic acid protection of a 17,20-glycol
  作者：George E. Joannou、Anthony Y. Reeder

  DOI：10.1016/0039-128x(95)00169-q

  日期：1996.1

  We report the synthesis of 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20- one (1) from 3 beta,15 beta-dihydroxy-5,16-pregnadien-20-one (11) in 7 steps using boronate derivatives as a means of protecting the 17,20-glycol side-chain of steroid intermediates. 16 alpha,17 alpha-Epoxy-3 beta,15 beta-dihydroxy-5- pregnen-20-one (12), an intermediate in the synthesis was prepared by epoxidation of 11 using

  我们报告了7个步骤由3 beta，15 beta-dihydroxy-5,16-pregnadien-20-one（11）合成3 beta，15 beta，17 alpha-trihydroxy-5-pregnen-20-一（1）使用硼酸酯衍生物作为保护类固醇中间体的17,20-二醇侧链的方法。通过使用氢氧化钠和过氧化氢的混合物将11进行环氧化，制备了16α，17α-环氧-3β，15β-二羟基-5-孕-20-（12）的中间体。用氢化锂铝还原12生成5-孕烯-3β，15β，17α，20（S + R）-四醇（13a和13b）的两种异构体，随后与正丁基硼酸反应生成5 -pregnene-3 beta，15 beta，17 alpha，20（S + R）-tetrol 17 alpha，20-butyl bornate（15a and 15b）。用乙酸酐和吡啶进行乙酰化，生成3个beta，15个b