methyl 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate | 153003-13-5

• 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: methyl 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(8R,9S,13S,14S,16R,17R)-3-acetyloxy-16-[tert-butyl(dimethyl)silyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]oxane-2-carboxylate
• CAS: 153003-13-5
• 化学式: C₃₉H₅₆O₁₃Si
• 分子量: 760.951
• InChiKey: PMOQQPHGTFVEMH-ZPFDPGIOSA-N

物化性质

• 沸点：
  707.9±60.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 在 sodium hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 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 、 无水碳酸镉 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 methyl 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate
  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