(22R)-2β,3β-Diacetoxy-14α,22,25-trihydroxy-6-oxo-Δ⁷-5β-cholestenin-(23) | 17131-90-7

• 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: (22R)-2β,3β-Diacetoxy-14α,22,25-trihydroxy-6-oxo-Δ⁷-5β-cholestenin-(23)
• CAS: 17131-90-7
• 化学式: C₃₁H₄₄O₈
• 分子量: 544.686
• InChiKey: KYSRQTXXFHFCDM-DBZRLZQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  130.36
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2β.3β-Diacetoxy-14α-hydroxy-6-oxo-Δ^7.22-5α-ergostadien 生成 (22R)-2β,3β-Diacetoxy-14α,22,25-trihydroxy-6-oxo-Δ⁷-5β-cholestenin-(23)
  参考文献：
  名称：

  Zur Synthese des Ecdysons IX. Mitteilung über Insektenhormone

  摘要：

  AbstractA synthesis of ecdysone is described by which the insect moulting hormone can be readily prepared. Oxidation of ergosterol gave the 6‐keto‐Δ7‐function, and preparation of the Δ2‐olefine followed by stereospecific hydroxylation led to the 2β,3β‐glycol system. Ozonization furnished (20 S)‐2β,3β‐diacetoxy‐20‐formyl‐5α‐pregn‐7‐en‐6‐one into which the side chain was introduced by a Grignard reaction with 2‐methyl‐3‐butyn‐2‐ol tetrahydropyran‐2‐yl ether and a subsequent reduction of the triple bond. Hydroxylation at C‐14 and isomerization at C‐5 gave ecdysone. By an interchange of the sequence of the reactions C‐22 isoecdysone was obtained stereospecifically.

  DOI：

  10.1002/hlca.19670500825