glycoursodeoxycholic acid 7-N-acetylglucosaminide | 145624-11-9

• 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: glycoursodeoxycholic acid 7-N-acetylglucosaminide
• 英文别名: N-Acetylglucosaminyl ursodeoxycholyl glycine；2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-7-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
• CAS: 145624-11-9
• 化学式: C₃₄H₅₆N₂O₁₀
• 分子量: 652.826
• InChiKey: LUKHXDHUMKXYJA-AZAFIUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  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