3,17β-diacetoxy-16α-hydroxyestra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside | 164468-83-1

• 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: 3,17β-diacetoxy-16α-hydroxyestra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside
• CAS: 164468-83-1
• 化学式: C₃₆H₄₇NO₁₄
• 分子量: 717.767
• InChiKey: ZAMHAVAGXXHUSO-SEEJDPADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  199.29
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3,17β-diacetoxy-16α-hydroxyestra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以35 mg的产率得到3,16α,17β-trihydroxyestra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-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
• 作为产物：
  描述：

  Oestratetraen-(1,3,5(10),15)-diol-(3,17β)-diacetat 在 无水碳酸镉 四氧化锇 作用下， 以 吡啶 、 甲苯 、 苯 为溶剂， 反应 72.0h， 生成 3,17β-diacetoxy-16α-hydroxyestra-1,3,5(10)-trien-15α-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