(20S)-21-Acetoxy-20-methyl-1,4-pregnadien-3-on | 80287-31-6

• 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: (20S)-21-Acetoxy-20-methyl-1,4-pregnadien-3-on
• CAS: 80287-31-6
• 化学式: C₂₄H₃₄O₃
• 分子量: 370.532
• InChiKey: WSGWKOJOTBVSSE-QMIPSKNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (20S)-21-Acetoxy-20-methyl-1,4-pregnadien-3-on 在 2,4,6-三甲基吡啶 、 甲醇 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 双氧水 、 lithium 、 氯化铵 、 对甲苯磺酸 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 甲苯 为溶剂， 反应 28.75h， 生成 (20S)-21-(1-Aethoxyaethoxy)-20-methyl-5-pregnen-1α,3β-diol
  参考文献：
  名称：

  EINE ergiebige Herstellung冯1α，3β二羟基Δ 5 -steroiden第三人以Reduktion冯1α，2α环氧-4,6-二烯-3- onen MIT锂在Ammoniak †

  摘要：

  用于制备1α，3β二羟基Δ的有效程序5个由1α还原，-steroids2α环氧-4,6-二烯-3-酮与锂在氨

  DOI：

  10.1002/hlca.19810640621
• 作为产物：
  描述：

  bisnoralcohol 在 4-二甲氨基吡啶 、 二苯基二硒醚 、 三乙胺 、 1-羟基-1,3-二氧代-1lambda5,2-苯并碘氧戊环-4-羧酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.75h， 生成 (20S)-21-Acetoxy-20-methyl-1,4-pregnadien-3-on
  参考文献：
  名称：

  Biocatalytic Steroidal 9α‐Hydroxylation and Fragmentation Enable the Concise Chemoenzymatic Synthesis of 9,10‐Secosteroids

  摘要：

  9,10‐Secosteroids are an important group of marine steroids with diverse biological activities. Herein, we report a chemoenzymatic strategy for the concise, modular, and scalable synthesis of ten naturally occurring 9,10‐secosteroids from readily available steroids in three to eight steps. The key feature lies in utilizing a Rieske oxygenase‐like 3‐ketosteroid 9α‐hydroxylase (KSH) as the biocatalyst to achieve efficient C9−C10 bond cleavage and A‐ring aromatization of tetracyclic steroids through 9α‐hydroxylation and fragmentation. With synthesized 9,10‐secosteroides, structure–activity relationship was evaluated based on bioassays in terms of previously unexplored anti‐infective activity. This study provides experimental evidence to support the hypothesis that the biosynthetic pathway through which 9,10‐secosteroids are formed in nature shares a similar 9α‐hydroxylation and fragmentation cascade. In addition to the development of a biomimetic approach for 9,10‐secosteroid synthesis, this study highlights the great potential of chemoenzymatic strategies in chemical synthesis.

  DOI：

  10.1002/anie.202319624

文献信息

• Weiss; Gaudig; Beckert, Synthesis, 1992, # 8, p. 751 - 752
  作者：Weiss、Gaudig、Beckert

  DOI：——

  日期：——
• Eine ergiebige Herstellung von 1α,3β-Dihydroxy-Δ⁵-steroiden durch Reduktion von 1α,2α-Epoxy-4,6-dien-3-onen mit Lithium in Ammoniak
  作者：Andor Fürst、Ludvik Labler、Werner Meier

  DOI：10.1002/hlca.19810640621

  日期：1981.9.23

  An Efficient Procedure for Preparing 1α,3β-Dihydroxy-Δ5-steroids by Reduction of 1α,2α-Epoxy-4,6-dien-3-ones with Lithium in Ammonia

  用于制备1α，3β二羟基Δ的有效程序5个由1α还原，-steroids2α环氧-4,6-二烯-3-酮与锂在氨
• Biocatalytic Steroidal 9α‐Hydroxylation and Fragmentation Enable the Concise Chemoenzymatic Synthesis of 9,10‐Secosteroids
  作者：Hanxin Song、Zeliang Zhang、Chunyang Cao、Zhijun Tang、Jinghan Gui、Wen Liu

  DOI：10.1002/anie.202319624

  日期：2024.4.15

  9,10‐Secosteroids are an important group of marine steroids with diverse biological activities. Herein, we report a chemoenzymatic strategy for the concise, modular, and scalable synthesis of ten naturally occurring 9,10‐secosteroids from readily available steroids in three to eight steps. The key feature lies in utilizing a Rieske oxygenase‐like 3‐ketosteroid 9α‐hydroxylase (KSH) as the biocatalyst to achieve efficient C9−C10 bond cleavage and A‐ring aromatization of tetracyclic steroids through 9α‐hydroxylation and fragmentation. With synthesized 9,10‐secosteroides, structure–activity relationship was evaluated based on bioassays in terms of previously unexplored anti‐infective activity. This study provides experimental evidence to support the hypothesis that the biosynthetic pathway through which 9,10‐secosteroids are formed in nature shares a similar 9α‐hydroxylation and fragmentation cascade. In addition to the development of a biomimetic approach for 9,10‐secosteroid synthesis, this study highlights the great potential of chemoenzymatic strategies in chemical synthesis.