7α-(Benzyloxy)-3β-(tetrahydropyranyloxy)cholestan-24ξ-ol | 166896-82-8

• 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: 7α-(Benzyloxy)-3β-(tetrahydropyranyloxy)cholestan-24ξ-ol
• 英文别名: (6R)-6-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-7-phenylmethoxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-ol
• CAS: 166896-82-8
• 化学式: C₃₉H₆₂O₄
• 分子量: 594.919
• InChiKey: OJJABTNRNCBFPH-XOTXRUMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  7α-(Benzyloxy)-3β-(tetrahydropyranyloxy)cholestan-24ξ-ol 在 咪唑 、 3 A molecular sieve 、 dipyridine chromium trioxide 、 sodium cyanoborohydride 、 magnesium bromide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane
  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 、 草酰氯 、 四丁基氟化铵 、 氢气 、 dipyridine chromium trioxide 、 sodium hydride 、 potassium tri-sec-butyl-borohydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 7α-(Benzyloxy)-3β-(tetrahydropyranyloxy)cholestan-24ξ-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

• Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine
  作者：Anthony D. Pechulis、Frank H. Bellevue、Christopher L. Cioffi、Sean G. Trapp、John P. Fojtik、Anthony A. McKitty、William A. Kinney、Leah L. Frye

  DOI：10.1021/jo00121a033

  日期：1995.8

  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.