3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-cholan-7β-ol | 303178-19-0

• 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-bisnor-5α-cholan-7β-ol
• 英文别名: 3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-chola-7β-ol
• CAS: 303178-19-0
• 化学式: C₃₀H₅₄O₄Si
• 分子量: 506.842
• InChiKey: KOWPUDSSCUPIDC-YLVJDXTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.02
• 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：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-cholan-7β-ol 在 盐酸 、 potassium tri-sec-butyl-borohydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 7α,22-dihydroxy-23,24-bisnor-5α-chola-3-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
• 作为产物：
  描述：

  3-dioxolane-23,24-bisnorchola-5-en-22-ol 在 ruthenium trichloride 、 platinum on activated charcoal 咪唑 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 氢气 作用下， 以 二氯甲烷 、 环己烷 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-cholan-7β-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

文献信息

• 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.