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 | 911358-00-4

• 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: 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
• CAS: 911358-00-4
• 化学式: C₃₄H₅₆N₂O₁₄S₂
• 分子量: 780.956
• InChiKey: KLRIUOUKRCSWSF-WRUOKHQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  272
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  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 在 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以32 mg的产率得到3β-sulfooxy-7β-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cholen-24-oyl taurine disodium salts
  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：

  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 sodium hydroxide 、 无水碳酸镉 、 4 A molecular sieve 、 对甲苯磺酸 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.17h， 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

文献信息

• 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.