3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-ol | 153003-12-4

• 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-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-ol
• CAS: 153003-12-4
• 化学式: C₂₆H₄₀O₄Si
• 分子量: 444.687
• InChiKey: FMMMZJYRZVVKSQ-CUMUNZOQSA-N

物化性质

• 沸点：
  511.3±50.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-ol 在 sodium hydroxide 、 无水碳酸镉 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 1,3,5[10]-雌甾三烯-3,16alpha,17beta-三羟基 17-葡糖苷酸
  参考文献：
  名称：

  The synthesis of estriol 16- and 17-monoglucuronide from estriol

  摘要：

  An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported.

  DOI：

  10.1016/0039-128x(93)90001-4
• 作为产物：
  描述：

  雌三醇 在 吡啶 作用下， 反应 0.5h， 生成 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-ol
  参考文献：
  名称：

  The synthesis of estriol 16- and 17-monoglucuronide from estriol

  摘要：

  An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported.

  DOI：

  10.1016/0039-128x(93)90001-4