3β-tert-butyldimethylsilyloxy-7α-hydroxyandrost-5-en-17-one | 1177400-13-3

• 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: 3β-tert-butyldimethylsilyloxy-7α-hydroxyandrost-5-en-17-one
• 英文别名: (3S,7S,8R,9S,10R,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 1177400-13-3
• 化学式: C₂₅H₄₂O₃Si
• 分子量: 418.692
• InChiKey: JRRUAZISELLNTA-OANIGTROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-tert-butyldimethylsilyloxy-7α-hydroxyandrost-5-en-17-one 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到3β-tert-butyldimethylsilyloxy-7α-chloroandrost-5-en-17-one
  参考文献：
  名称：

  Synthesis of 3β-hydroxy-androsta-5,7-dien-17-one from 3β-hydroxyandrost-5-en-17-one via microbial 7α-hydroxylation

  摘要：

  The synthesis of 3 beta-hydroxy-androsta-5,7-dien-17-one from 3 beta-hydroxy-androst-5-en-17-one (dehydroepiandrosterone, DHEA) via microbial 7 alpha-hydroxylation has been accomplished. At the first stage, 3 beta,7 alpha-dihydroxy-androst-5-en-17-one was obtained in high yield (71.2%) using a strain of Gibberella zeae VKM F-2600, which was first applied for DHEA conversion. The further route included the substitution of 7 alpha-hydroxyl group with chlorine followed by a dehydrochlorination stage, and required minimal purifications of the intermediate products. The steroids obtained at every step were characterized by TLC. H-1 NMR, MS, UV- and IR-spectrometry.The combination of microbial and chemical steps ensured 54.6% yield of the target 3 beta-hydroxyandrosta-5,7-dien-17-one from DHEA and can be applied for obtaining novel vitamin D derivatives. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.10.019
• 作为产物：
  描述：

  去氢表雄酮 、 叔丁基二甲基氯硅烷 在 randomly methylated β-cyclodextrin 、 吡啶 作用下， 以 水 、 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 54.0h， 以3.50 g的产率得到3β-tert-butyldimethylsilyloxy-7α-hydroxyandrost-5-en-17-one
  参考文献：
  名称：

  Synthesis of 3β-hydroxy-androsta-5,7-dien-17-one from 3β-hydroxyandrost-5-en-17-one via microbial 7α-hydroxylation

  摘要：

  The synthesis of 3 beta-hydroxy-androsta-5,7-dien-17-one from 3 beta-hydroxy-androst-5-en-17-one (dehydroepiandrosterone, DHEA) via microbial 7 alpha-hydroxylation has been accomplished. At the first stage, 3 beta,7 alpha-dihydroxy-androst-5-en-17-one was obtained in high yield (71.2%) using a strain of Gibberella zeae VKM F-2600, which was first applied for DHEA conversion. The further route included the substitution of 7 alpha-hydroxyl group with chlorine followed by a dehydrochlorination stage, and required minimal purifications of the intermediate products. The steroids obtained at every step were characterized by TLC. H-1 NMR, MS, UV- and IR-spectrometry.The combination of microbial and chemical steps ensured 54.6% yield of the target 3 beta-hydroxyandrosta-5,7-dien-17-one from DHEA and can be applied for obtaining novel vitamin D derivatives. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.10.019

文献信息

• Synthesis of 3β-hydroxy-androsta-5,7-dien-17-one from 3β-hydroxyandrost-5-en-17-one via microbial 7α-hydroxylation
  作者：Tatyana G. Lobastova、Sergey M. Khomutov、Ljudmila L. Vasiljeva、Margarita A. Lapitskaya、Kasimir K. Pivnitsky、Marina V. Donova

  DOI：10.1016/j.steroids.2008.10.019

  日期：2009.2

  The synthesis of 3 beta-hydroxy-androsta-5,7-dien-17-one from 3 beta-hydroxy-androst-5-en-17-one (dehydroepiandrosterone, DHEA) via microbial 7 alpha-hydroxylation has been accomplished. At the first stage, 3 beta,7 alpha-dihydroxy-androst-5-en-17-one was obtained in high yield (71.2%) using a strain of Gibberella zeae VKM F-2600, which was first applied for DHEA conversion. The further route included the substitution of 7 alpha-hydroxyl group with chlorine followed by a dehydrochlorination stage, and required minimal purifications of the intermediate products. The steroids obtained at every step were characterized by TLC. H-1 NMR, MS, UV- and IR-spectrometry.The combination of microbial and chemical steps ensured 54.6% yield of the target 3 beta-hydroxyandrosta-5,7-dien-17-one from DHEA and can be applied for obtaining novel vitamin D derivatives. (C) 2008 Elsevier Inc. All rights reserved.