3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-chola-7-one | 208833-63-0

• 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-chola-7-one
• 英文别名: 3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnor-5α-cholan-7-one
• CAS: 208833-63-0
• 化学式: C₃₀H₅₂O₄Si
• 分子量: 504.826
• InChiKey: VYKNBJCETKWLFT-FJGFVRQASA-N

物化性质

• 沸点：
  539.861±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.050±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 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：
  0.97
• 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-bisnor-5α-chola-7-one 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 36.25h， 生成 3β-N-1-[N-(3-[4-aminobutyl])-1,3-diaminopropyldicarbamate]-7α,22-dihydroxy-23,24-bisnor-5α-cholane 22-sulfate trihydrochloride
  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-chola-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

• Synthesis and antimicrobial activity of 7α-amino-23,24-bisnor-5α-cholan-22-ol derivatives
  作者：Sharaf Nawaz Khan、Young Mee Jung、Bong Jin Kim、Heeyeong Cho、Jinho Lee、Hong-Seok Kim

  DOI：10.1016/j.bmcl.2008.03.042

  日期：2008.4

  A series of 7 alpha-aminobisnorsteroids were synthesized and their in vitro antimicrobial activity was evaluated regarding Gram-positive and Gram-negative bacteria. The stereoselective reductive amination of 7-ketosteroid 3 with NH4OAc, in the presence of NaBH3CN, afforded a high yield of 7 alpha-aminosteroid 4. The 3,7-diaminobisnorsteroids were obtained by the reductive amination of 4 with NH4OTf, Boc-spermidine, and Boc-spermine. 3 alpha,7 alpha-Diaminobisnorsterol dihydrochloride 15 showed the highest antimicrobial activity against Streptococcus pyogenes 308A with a MIC value of 1.6 mu g/mL. Hemolytic activities of the compounds 13-20 were determined. Compound 13 showed MHC value at 100 mu g/mL. (c) 2008 Elsevier Ltd. All rights reserved.
• 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.