methyl 7β-hydroxy-3-oxo-5β-cholan-24-oate 7-N-acetylglucosaminide triacetate | 145624-06-2

• 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 7β-hydroxy-3-oxo-5β-cholan-24-oate 7-N-acetylglucosaminide triacetate
• CAS: 145624-06-2
• 化学式: C₃₉H₅₉NO₁₂
• 分子量: 733.897
• InChiKey: JABORHMEAFTKBU-RNESDMKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  52.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 7β-hydroxy-3-oxo-5β-cholan-24-oate 7-N-acetylglucosaminide triacetate 在 氢氧化钾 、 sodium tetrahydroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 5.5h， 生成 glycoursodeoxycholic acid 7-N-acetylglucosaminide
  参考文献：
  名称：

  Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids

  摘要：

  3-N-Acetylglucosaminides of unconjugated, glycine- and taurine-conjugated bile acids have been synthesized. Bile acids appropriately protected were condensed with acetochloroglucosamine through the 3 alpha-hydroxyl group by means of the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. Subsequent borohydride reduction and/or alkaline hydrolysis provided desired 3-N-acetylglucosaminides of unconjugated bile acids. Glycine-conjugates were obtained from N-acetylglucosaminides of unconjugated bile acids and ethyl glycinate by the carbodiimide method. The preparation of N-acetylglucosaminides of taurine-conjugates was attained by the Koenigs-Knorr reaction of bile acid p-nitrophenyl esters followed by condensation with taurine. 7-N-Acetylglucosaminides of ursodeoxycholates were prepared in a similar fashion. The convenient synthesis of 3-N-acetylglucosaminides of unconjugated bile acids is also described.

  DOI：

  10.1016/0039-128x(92)90021-z
• 作为产物：
  描述：

  methyl 3-oxo-7β-hydroxy-5β-cholan-24-oate 、 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 8.0h， 以80 mg的产率得到methyl 7β-hydroxy-3-oxo-5β-cholan-24-oate 7-N-acetylglucosaminide triacetate
  参考文献：
  名称：

  Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids

  摘要：

  3-N-Acetylglucosaminides of unconjugated, glycine- and taurine-conjugated bile acids have been synthesized. Bile acids appropriately protected were condensed with acetochloroglucosamine through the 3 alpha-hydroxyl group by means of the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. Subsequent borohydride reduction and/or alkaline hydrolysis provided desired 3-N-acetylglucosaminides of unconjugated bile acids. Glycine-conjugates were obtained from N-acetylglucosaminides of unconjugated bile acids and ethyl glycinate by the carbodiimide method. The preparation of N-acetylglucosaminides of taurine-conjugates was attained by the Koenigs-Knorr reaction of bile acid p-nitrophenyl esters followed by condensation with taurine. 7-N-Acetylglucosaminides of ursodeoxycholates were prepared in a similar fashion. The convenient synthesis of 3-N-acetylglucosaminides of unconjugated bile acids is also described.

  DOI：

  10.1016/0039-128x(92)90021-z