benzyl N-[[(8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methyl-17-oxo-6,7,8,9,11,12-hexahydrocyclopenta[a]phenanthren-14-yl]oxy]carbamate | 181866-43-3

• 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: benzyl N-[[(8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methyl-17-oxo-6,7,8,9,11,12-hexahydrocyclopenta[a]phenanthren-14-yl]oxy]carbamate
• CAS: 181866-43-3
• 化学式: C₃₂H₄₁NO₅Si
• 分子量: 547.767
• InChiKey: DQCKGFMRTNDPII-ITWZUIQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[[(8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methyl-17-oxo-6,7,8,9,11,12-hexahydrocyclopenta[a]phenanthren-14-yl]oxy]carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以88%的产率得到(8R,9S,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  5-(Trimethylstannyl)-2H-pyran-2-one and 3-(Trimethylstannyl)-2H-pyran-2-one:  New 2H-Pyran-2-one Synthons

  摘要：

  5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively, This reaction is applicable to the enol triflates of 14 beta-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.

  DOI：

  10.1021/jo951394t
• 作为产物：
  描述：

  3-(O-tert-butyl(dimethyl)silyl)estrone 在 甲醇 、 palladium diacetate 、 正丁基锂 、 对甲苯磺酸 、 二异丙胺 作用下， 以 苯甲腈 为溶剂， 反应 58.83h， 生成 benzyl N-[[(8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methyl-17-oxo-6,7,8,9,11,12-hexahydrocyclopenta[a]phenanthren-14-yl]oxy]carbamate
  参考文献：
  名称：

  5-(Trimethylstannyl)-2H-pyran-2-one and 3-(Trimethylstannyl)-2H-pyran-2-one:  New 2H-Pyran-2-one Synthons

  摘要：

  5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively, This reaction is applicable to the enol triflates of 14 beta-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.

  DOI：

  10.1021/jo951394t

文献信息

• 5-(Trimethylstannyl)-2<i>H</i>-pyran-2-one and 3-(Trimethylstannyl)-2<i>H</i>-pyran-2-one:  New 2<i>H</i>-Pyran-2-one Synthons
  作者：Zhi Liu、Jerrold Meinwald

  DOI：10.1021/jo951394t

  日期：1996.1.1

  5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively, This reaction is applicable to the enol triflates of 14 beta-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.