3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnorchola-5-en-7-one | 202817-33-2

• 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: 3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnorchola-5-en-7-one
• 英文别名: 3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-binorchola-5-en-7-one；(8'S,9'S,10'R,13'R,14'S,17'R)-17'-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene]-7'-one
• CAS: 202817-33-2
• 化学式: C₃₀H₅₀O₄Si
• 分子量: 502.81
• InChiKey: OJIQPPKNMRNKTA-SBQXNPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnorchola-5-en-7-one 在 platinum on activated charcoal 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 44.0h， 生成 3-β-amino-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-chola-7α-ol
  参考文献：
  名称：

  Synthesis and antimicrobial activity of squalamine analogue

  摘要：

  Synthesis and antimicrobial activity of squalamine analogue 2 are reported. The synthesis of 2 was accomplished from bisnoralcohol 3. The spermidine moiety was introduced via reductive amination of an appropriately functionalized 3 beta-aminosterol with spermidinyl aldehyde 17 utilizing sodium triacetoxyborohydride as the reducing agent. Compound 2 shows weaker antimicrobial activity than squalamine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00128-0
• 作为产物：
  描述：

  3-dioxolane-23,24-bisnorchola-5-en-22-ol 在 ruthenium trichloride 咪唑 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 26.0h， 生成 3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnorchola-5-en-7-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of squalamine analogue

  摘要：

  Synthesis and antimicrobial activity of squalamine analogue 2 are reported. The synthesis of 2 was accomplished from bisnoralcohol 3. The spermidine moiety was introduced via reductive amination of an appropriately functionalized 3 beta-aminosterol with spermidinyl aldehyde 17 utilizing sodium triacetoxyborohydride as the reducing agent. Compound 2 shows weaker antimicrobial activity than squalamine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00128-0

文献信息

• Some Reaction Safety Aspects of Ruthenium-Catalyzed Allylic Oxidations of Δ-5-Steroids in the Pilot Plant
  作者：Michael Harre、Reinhard Haufe、Klaus Nickisch、Peter Weinig、Hilmar Weinmann、William A. Kinney、Xuehai Zhang

  DOI：10.1021/op9700587

  日期：1998.3.1

  The ruthenium-catalyzed allylic oxidation of Delta-5-steroids with tert-butyl hydroperoxide to the corresponding unsaturated ketones was studied. During the scale-up to the pilot plant level, serious safety problems were detected, and the identified runaway potential of this reaction was studied. By modifying the original oxidation procedure, it was possible to establish this reaction safely in the pilot plant at 17-kg scale. Furthermore, the procedure was applied successfully to several other steroids on the laboratory scale.
• Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids
  作者：Sharaf Nawaz Khan、Bong Jin Kim、Hong-Seok Kim

  DOI：10.1016/j.bmcl.2007.07.001

  日期：2007.9

  A series of 7-fluoro-3-aminosteroids were synthesized and their in vitro antimicrobial activities were evaluated against Gram-positive and Gram-negative bacteria. The nucleophilic fluorination of several 7 beta-hydroxysteroids by diethylaminosulfur trifluoride in n-pentane, followed by reductive amination of the resulting 7-fluoro-3-ketosteroids with spermidine in the presence of NaBH3CN, afforded 7-fluoro-3-aminosteroids in high yield. Compound 25 showed the highest antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Streptococcus pyogenes, and Escherichia coli. (c) 2007 Elsevier Ltd. All rights reserved.