Oestratrien-(1,3,5(10))-tetraol-(3,15α,16α,17β)-tetraacetat | 16934-35-3

• 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: Oestratrien-(1,3,5(10))-tetraol-(3,15α,16α,17β)-tetraacetat
• 英文别名: [(8R,9S,13S,14S,15R,16R,17R)-3,16,17-triacetyloxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-15-yl] acetate
• CAS: 16934-35-3
• 化学式: C₂₆H₃₂O₈
• 分子量: 472.535
• InChiKey: HNAUOWNXZCSLRO-HYFKJDSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Oestratrien-(1,3,5(10))-tetraol-(3,15α,16α,17β)-tetraacetat 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 生成 (15α,16α,17β)-3-hydroxyestra-1,3,5(10)-triene-15,16,17-triyl triacetate
  参考文献：
  名称：

  Syntheses of estetrol mqnoglucuronides

  摘要：

  Four possible monoglucuronides of estetrol (estra-1,3,5(10)-triene-3,15 alpha, 16 alpha, 17 beta-tetraol) have been prepared from appropriately protected estetrol by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Condensation of methyl acetobromoglucuronate with estetrol 15,16,17-triacetate provided the 3-glucuronide acetate-methyl ester in a satisfactory yield. Introduction of the glucuronyl residue into C-17 was similarly attained by the use of estetrol 3-benzoate 15,16-acetonide. When estetrol 3,17-diacetate and acetobromosugar were stirred in anhydrous toluene in the presence of cadmium salt, the reaction occurred at C-16 and C-15 yielding two isomeric monoglucuronide derivatives in a ratio of ca. 5 to 2. Removal of the protecting groups in the four glucuronide acetate-methyl esters gave the desired estetrol glucuronides, respectively. These synthetic substrates underwent readily enzymatic hydrolysis with beef-liver beta-glucuronidase to afford estetrol.

  DOI：

  10.1016/0039-128x(76)90072-6

文献信息

• Preparation of tritium labelled estetrol [estra-1,3,5(10)- triene-3,15α,16α,17β- tetrol 6,7-3H]
  作者：Jack Fishman、Henry Guzik

  DOI：10.1002/jlcr.2590060406

  日期：1970.10

  The preparation of the tritium labelled fetal metabolite estra-1, 3, 5 (10)-3, 15α, 16α, 17β-tetrol 6,7-3H is described. The material was prepared by oxidation of the tetrol tetraacetate lb to the 6-keto derivative II. Reduction of the 6-ketone to the 6-hydroxy compound III and dehydration with dimethylsulfoxide gave the Δ6 derivative III. Reduction of III with tritium followed by hydrolysis gave the tetrol-3H with a specific activity of 43 curies/mmole.