3β-hydroxy-7-oxo-5-cholen-24-oic acid | 25218-38-6

• 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: 3β-hydroxy-7-oxo-5-cholen-24-oic acid
• 英文别名: 3β-hydroxy-7-oxo-cholen-(5)-oic acid-(24)；3β-Hydroxy-7-oxo-cholen-(5)-saeure-(24)；3beta-Hydroxy-7-oxochol-5-en-24-oic Acid；(4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 25218-38-6
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: JHFXTNJNQOZGEJ-HICUSVRDSA-N

物化性质

• 沸点：
  565.9±33.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  乙腈：1mg/mL；乙醇：1mg/mL；甲醇：1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-7-oxo-5-cholen-24-oic acid 在 咪唑 、 sodium hydroxide 、 无水碳酸镉 、 zinc(II) tetrahydroborate 、 4 A molecular sieve 、 对甲苯磺酸 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 45.67h， 生成 2-[[(4R)-4-[(3S,7R,8S,9S,10R,13R,14S,17R)-7-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10,13-dimethyl-3-sulfooxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
  参考文献：
  名称：

  Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1

  摘要：

  The chemical synthesis of 3 beta,7 beta-dihydroxy-S-cholen-24-oic acid, triply conjugated by sulfuric acid at C-3, by N-acetylglucosamine (GlcNAc) at C-7, and by glycine or taurine at C-24, is described. These are unusual, major metabolites of bile acid found to be excreted in the urine of a patient with Niemann-Pick disease type C1. Analogous double - conjugates of 3 beta-hydroxy-7-oxo-5-cholen-24-oic acid were also prepared. The principal reactions involved were: (1) beta-D-N-acetylglucosaminidation at C-7 of methyl 3 beta-tert-butyldimethylsilyloxy (TBDMSi)-7 beta-hydroxy-5-cholen-24-oate with 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-tri-O-acetyl-D-glucopyranose in the presence of CdCO3 in boiling toluene; (2) sulfation at C-3 of the resulting 3 beta-TBDMSi-7 beta-GlcNAc with sulfur trioxide-trimethylamine complex in pyridine; and (3) direct amidation at C-24 of the 3 beta-sulfooxy-7 beta-GlcNAc conjugate with glycine methyl ester hydrochloride (or taurine) using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as a coupling agent in DMF. The structures of the multi-conjugated bile acids were characterized by liquid chromatography-mass spectrometry with an electrospray ionization probe under the positive and negative ionization modes. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.07.008
• 作为产物：
  描述：

  猪去氧胆酸甲酯 在 吡啶 、 叔丁基过氧化氢 、 氢氧化钾 、 重铬酸吡啶 、 Celite 、 potassium acetate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 105.0h， 生成 3β-hydroxy-7-oxo-5-cholen-24-oic acid
  参考文献：
  名称：

  Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1

  摘要：

  The chemical synthesis of 3 beta,7 beta-dihydroxy-S-cholen-24-oic acid, triply conjugated by sulfuric acid at C-3, by N-acetylglucosamine (GlcNAc) at C-7, and by glycine or taurine at C-24, is described. These are unusual, major metabolites of bile acid found to be excreted in the urine of a patient with Niemann-Pick disease type C1. Analogous double - conjugates of 3 beta-hydroxy-7-oxo-5-cholen-24-oic acid were also prepared. The principal reactions involved were: (1) beta-D-N-acetylglucosaminidation at C-7 of methyl 3 beta-tert-butyldimethylsilyloxy (TBDMSi)-7 beta-hydroxy-5-cholen-24-oate with 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-tri-O-acetyl-D-glucopyranose in the presence of CdCO3 in boiling toluene; (2) sulfation at C-3 of the resulting 3 beta-TBDMSi-7 beta-GlcNAc with sulfur trioxide-trimethylamine complex in pyridine; and (3) direct amidation at C-24 of the 3 beta-sulfooxy-7 beta-GlcNAc conjugate with glycine methyl ester hydrochloride (or taurine) using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as a coupling agent in DMF. The structures of the multi-conjugated bile acids were characterized by liquid chromatography-mass spectrometry with an electrospray ionization probe under the positive and negative ionization modes. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.07.008

文献信息

• 43. Derivatives of cis-3-hydroxy-Δ⁵-cholenic acid
  作者：G. A. D. Haslewood

  DOI：10.1039/jr9380000224

  日期：——
• DIAGNOSTIC METHODS AND KITS
  申请人：Cholestenix Limited

  公开号：EP3345004B1

  公开（公告）日：2020-07-22
• Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1
  作者：Takashi Iida、Genta Kakiyama、Yohei Hibiya、Shohei Miyata、Takehiko Inoue、Kohsaku Ohno、Takaaki Goto、Nariyasu Mano、Junichi Goto、Toshio Nambara、Alan F. Hofmann

  DOI：10.1016/j.steroids.2005.07.008

  日期：2006.1

  The chemical synthesis of 3 beta,7 beta-dihydroxy-S-cholen-24-oic acid, triply conjugated by sulfuric acid at C-3, by N-acetylglucosamine (GlcNAc) at C-7, and by glycine or taurine at C-24, is described. These are unusual, major metabolites of bile acid found to be excreted in the urine of a patient with Niemann-Pick disease type C1. Analogous double - conjugates of 3 beta-hydroxy-7-oxo-5-cholen-24-oic acid were also prepared. The principal reactions involved were: (1) beta-D-N-acetylglucosaminidation at C-7 of methyl 3 beta-tert-butyldimethylsilyloxy (TBDMSi)-7 beta-hydroxy-5-cholen-24-oate with 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-tri-O-acetyl-D-glucopyranose in the presence of CdCO3 in boiling toluene; (2) sulfation at C-3 of the resulting 3 beta-TBDMSi-7 beta-GlcNAc with sulfur trioxide-trimethylamine complex in pyridine; and (3) direct amidation at C-24 of the 3 beta-sulfooxy-7 beta-GlcNAc conjugate with glycine methyl ester hydrochloride (or taurine) using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as a coupling agent in DMF. The structures of the multi-conjugated bile acids were characterized by liquid chromatography-mass spectrometry with an electrospray ionization probe under the positive and negative ionization modes. (c) 2005 Elsevier Inc. All rights reserved.