tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(3-(((3S,5R,7S,8R,9S,10S,13R,14S,17R)-7-fluoro-17-((S)-1-hydroxypropan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)amino)propyl)carbamate | 952305-48-5

• 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: tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(3-(((3S,5R,7S,8R,9S,10S,13R,14S,17R)-7-fluoro-17-((S)-1-hydroxypropan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)amino)propyl)carbamate
• CAS: 952305-48-5
• 化学式: C₃₉H₇₀FN₃O₅
• 分子量: 680.0
• InChiKey: JQDCPJHJAWURJZ-YQGJQSRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  100.13
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(3-(((3S,5R,7S,8R,9S,10S,13R,14S,17R)-7-fluoro-17-((S)-1-hydroxypropan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)amino)propyl)carbamate 在 pyridine-SO3 complex 作用下， 反应 4.0h， 以95%的产率得到(S)-2-((3S,5R,7S,8R,9S,10S,13R,14S,17R)-3-((3-((tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)amino)butyl)amino)propyl)amino)-7-fluoro-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propyl hydrogen sulfate
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.07.001
• 作为产物：
  描述：

  3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnorchola-5-en-7-one 在 乙醇 、 二乙胺基三氟化硫 、 lithium 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 氨 、 丙酮 、 正戊烷 为溶剂， 反应 7.5h， 生成 tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(3-(((3S,5R,7S,8R,9S,10S,13R,14S,17R)-7-fluoro-17-((S)-1-hydroxypropan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)amino)propyl)carbamate
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.07.001