24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7α-ol | 166896-78-2

• 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: 24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7α-ol
• 英文别名: 24-t-Butyldimethylsilyloxy-3beta-tetrahydropyranyloxy-5alpha-cholan-7alpha-ol；(3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-[tert-butyl(dimethyl)silyl]oxypentan-2-yl]-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
• CAS: 166896-78-2
• 化学式: C₃₅H₆₄O₄Si
• 分子量: 576.976
• InChiKey: WXAUAXUIJYSCPW-OERRTJOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7α-ol 在 palladium on activated charcoal 吡啶 、 咪唑 、 盐酸 、 草酰氯 、 pyridine-SO3 complex 、 3 A molecular sieve 、 四丁基氟化铵 、 氢气 、 dipyridine chromium trioxide 、 sodium hydride 、 sodium cyanoborohydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三氟乙酸 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， -78.0~40.0 ℃ 、379.21 kPa 条件下， 反应 97.75h， 生成 24ξ-Squalamine
  参考文献：
  名称：

  Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine

  摘要：

  Squalamine (1) is a novel steroidal polyamine which exhibits broad spectrum anti-infective activity. It inhibits the growth of bacteria, both Gram positive and Gram negative, and fungi. The synthesis of 24 xi-squalamine was accomplished in 17 steps from 3 beta-hydroxy-5-cholenic acid. The stereospecific introduction of the 7 alpha-hydroxyl group was achieved by allylic oxidation followed by hydrogenation of the Delta(5) olefin and reduction of the 7-keto group with K-selectride. The polyamine side chain was introduced via reductive amination of an appropriately functionalized 3-keto steroid with a suitably protected spermidine utilizing sodium cyanoborohydride as the reducing agent. The required 24-sulfate was introduced by selective sulfation of the 7 alpha,24 xi-diol with sulfur trioxide-pyridine complex.

  DOI：

  10.1021/jo00121a033
• 作为产物：
  描述：

  3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol 在 platinum(IV) oxide 咪唑 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 氢气 、 dipyridine chromium trioxide 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.5h， 生成 24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)-5α-cholan-7α-ol
  参考文献：
  名称：

  Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine

  摘要：

  Squalamine (1) is a novel steroidal polyamine which exhibits broad spectrum anti-infective activity. It inhibits the growth of bacteria, both Gram positive and Gram negative, and fungi. The synthesis of 24 xi-squalamine was accomplished in 17 steps from 3 beta-hydroxy-5-cholenic acid. The stereospecific introduction of the 7 alpha-hydroxyl group was achieved by allylic oxidation followed by hydrogenation of the Delta(5) olefin and reduction of the 7-keto group with K-selectride. The polyamine side chain was introduced via reductive amination of an appropriately functionalized 3-keto steroid with a suitably protected spermidine utilizing sodium cyanoborohydride as the reducing agent. The required 24-sulfate was introduced by selective sulfation of the 7 alpha,24 xi-diol with sulfur trioxide-pyridine complex.

  DOI：

  10.1021/jo00121a033

文献信息

• Aminosterol compounds and a method of treating infection using the
  申请人：Magainin Pharmaceuticals Inc.

  公开号：US05840740A1

  公开（公告）日：1998-11-24

  Disclosed are aminosterol compounds 1360 and 1361: ##STR1## which can be obtained in isolated or purified form from the liver of the dogfish shark.

  揭示了两种氨基固醇化合物1360和1361：##STR1## 可以从鲨鱼的肝脏中以分离或纯化形式获得。