Oestratetraen-(1,3,5(10),15)-diol-(3,17β)-diacetat | 16127-98-3

• 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: Oestratetraen-(1,3,5(10),15)-diol-(3,17β)-diacetat
• 英文别名: [(8R,9S,13S,14S,17S)-3-acetyloxy-13-methyl-6,7,8,9,11,12,14,17-octahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 16127-98-3
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: ORFGIQUKBMVXDG-AANPDWTMSA-N

物化性质

• 沸点：
  463.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Oestratetraen-(1,3,5(10),15)-diol-(3,17β)-diacetat 在 无水碳酸镉 吡啶 、 四氧化锇 作用下， 以 吡啶 、 甲苯 、 苯 为溶剂， 反应 72.0h， 生成 3,15α,17β-triacetoxyestra-1,3,5(10)-trien-16α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 15α-hydroxyestrogen 15-N-acetylglucosaminides

  摘要：

  The synthesis of 15-N-acetylglucosaminides of 15 alpha-hydroxyestrone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) is described. The latter two were prepared by condensation of 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-trio-O-acetyl-D-glucopyranose with appropriately protected 15 alpha-hydroxyestrogens by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Subsequent removal of protecting groups with methanolic potassium hydroxide provided the desired conjugates. 15 alpha-Hydroxyestrone 15-N-acetylglucosaminide was synthesized from the corresponding 15 alpha-hydroxyestradiol derivative by Jones oxidation followed by brief alkaline hydrolysis. These conjugates underwent enzymatic hydrolysis with beta-N-acetylglucosaminidase from Jack beans to produce 15 alpha-hydroxyestrogens.

  DOI：

  10.1016/0039-128x(94)00054-g

文献信息

• INDUSTRIAL PROCESS FOR THE PREPARATION OF HIGH PURITY ESTETROL
  申请人：Richter Gedeon Nyrt.

  公开号：EP3877395B1

  公开（公告）日：2022-12-07
• [EN] INDUSTRIAL PROCESS FOR THE PREPARATION OF HIGH PURITY ESTETROL<br/>[FR] PROCÉDÉ INDUSTRIEL POUR LA PRÉPARATION D'ESTÉTROL DE PURETÉ ÉLEVÉE
  申请人：RICHTER GEDEON NYRT

  公开号：WO2021044302A1

  公开（公告）日：2021-03-11

  The invention relates to the preparation of estetrol of formula (I), derivatives thereof protected at positions 3,15α,16α,17β of general formula (III), and 3-hydroxy derivatives thereof protected at positions 15α,16α,17β of general formula (IV), and to the intermediates of general formulae (III) and (IV) applied in the process. Another aspect of the invention is the use of estetrol of formula (I) obtained by the process of the invention for the preparation of a pharmaceutical composition.