3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside | 164468-85-3

• 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: 3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside
• CAS: 164468-85-3
• 化学式: C₄₄H₇₁NO₁₁Si₂
• 分子量: 846.219
• InChiKey: OIQRIYJOWSULNG-PVZSGMMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  58.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  144.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-yl-2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranoside 在 盐酸 、 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.58h， 生成 3-hydroxy-17-oxoestra-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
• 作为产物：
  描述：

  3,17β-bis(tert-butyldimethylsilyloxy)-estra-1,3,5(10)-trien-15α-ol 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 无水碳酸镉 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以20%的产率得到3,17β-bis(tert-butyldimethylsilyloxy)-estra-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