deoxycholic acid acyl glucuronide

• 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: deoxycholic acid acyl glucuronide
• 英文别名: 1-O-(3alpha,12alpha-dihydroxy-24-oxo-5beta-cholan-24-yl)-beta-D-glucopyranuronic acid；(2S,3S,4S,5R,6S)-6-[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-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]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₃₀H₄₈O₁₀
• 分子量: 568.705
• InChiKey: MZVCLCMWDVOQAH-GYSLYLNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 25.0 ℃ 、500.0 MPa 条件下， 反应 15.0h， 生成 deoxycholic acid acyl glucuronide
  参考文献：
  名称：

  Synthesis of Bile Acid 24-acyl Glucuronides

  摘要：

  The synthesis of acyl glucuronides of common bile acids is described By means of the Mitsunobu reaction employing diethylazodicarboxylate and triphenylphosphine, bile acids were condensed through the inherent C-24 carboxy group with benzyl,2,3,4-tri-O-benzyl-D-glucopyranuronate which was prepared from 1-O-methyl-alpha-D-glucose, The separation and purification of the beta-anomers at the anomeric position of the sugar moiety were attained by preparative thin-layer chromatography and/or high-performance liquid chromatography on a column packed with phenyl-bonded silica using H2O-MeOH as a mobile phase. The removal of the benzyl group on the sugar moiety was achieved by catalytic hydrogenation,with 10% palladium on carbon to yield the desired acyl glucuronides of bile acids. The structures of these acyl glucuronides were confirmed by proton nuclear magnetic resonance spectral properties. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00160-8

文献信息

• Synthesis of Bile Acid 24-acyl Glucuronides
  作者：Junichi Goto、Naoaki Murao、Junji Oohashi、Shigeo Ikegawa

  DOI：10.1016/s0039-128x(97)00160-8

  日期：1998.4

  The synthesis of acyl glucuronides of common bile acids is described By means of the Mitsunobu reaction employing diethylazodicarboxylate and triphenylphosphine, bile acids were condensed through the inherent C-24 carboxy group with benzyl,2,3,4-tri-O-benzyl-D-glucopyranuronate which was prepared from 1-O-methyl-alpha-D-glucose, The separation and purification of the beta-anomers at the anomeric position of the sugar moiety were attained by preparative thin-layer chromatography and/or high-performance liquid chromatography on a column packed with phenyl-bonded silica using H2O-MeOH as a mobile phase. The removal of the benzyl group on the sugar moiety was achieved by catalytic hydrogenation,with 10% palladium on carbon to yield the desired acyl glucuronides of bile acids. The structures of these acyl glucuronides were confirmed by proton nuclear magnetic resonance spectral properties. (C) 1998 by Elsevier Science Inc.