甲基(3alpha,5beta,7alpha)-7-乙酰氧基-3-羟基-12-氧代胆烷-24-酸酯 | 71837-87-1

• 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
• 中文名称: 甲基(3alpha,5beta,7alpha)-7-乙酰氧基-3-羟基-12-氧代胆烷-24-酸酯
• 中文别名: a-L-吡喃甘露糖苷,2-丙烯-1-基6-脱氧-2,3-O-(1-甲基亚乙基)-
• 英文名称: methyl 3α-hydroxy-7α-acetoxy-12-oxocholanate
• 英文别名: methyl-12-dehydrocholate 7-acetate；7α-acetoxy-3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester；7α-Acetoxy-3α-hydroxy-12-oxo-5β-cholan-24-saeure-methylester；3α-Hydroxy-7α-acetoxy-12-oxo-5β-cholansaeure-(24)-methylester；methyl (3α,5β,7α)-7-acetoxy-3-hydroxy-12-oxocholan-24-oate；Methyl (3alpha,5beta,7alpha)-7-acetoxy-3-hydroxy-12-oxocholan-24-oate；methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-acetyloxy-3-hydroxy-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 71837-87-1
• 化学式: C₂₇H₄₂O₆
• 分子量: 462.627
• InChiKey: MWUBEKFSCVGPKW-OYYDADKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基(3alpha,5beta,7alpha)-7-乙酰氧基-3-羟基-12-氧代胆烷-24-酸酯 在 氢氧化钾 、 乙二醇 作用下， 生成 鹅去氧胆酸
  参考文献：
  名称：

  Oxidation of Steroids. III. Selective Oxidations and Acylations in the Bile Acid Series¹

  摘要：

  DOI：

  10.1021/ja01168a046
• 作为产物：
  描述：

  胆酸甲酯 在 吡啶 、 盐酸 、 potassium chromate 、 溶剂黄146 、 苯 作用下， 生成 甲基(3alpha,5beta,7alpha)-7-乙酰氧基-3-羟基-12-氧代胆烷-24-酸酯
  参考文献：
  名称：

  Oxidation of Steroids. III. Selective Oxidations and Acylations in the Bile Acid Series¹

  摘要：

  DOI：

  10.1021/ja01168a046

文献信息

• Studies on analysis of bile acids. Preparation of 3-glucuronides of 7- and 12-oxo bile acids.
  作者：JUNICHI GOTO、KAZUHIKO SUZAKI、TOSHIO NAMBARA

  DOI：10.1248/cpb.30.4422

  日期：——

  The 3-glucuronides of unconjugated and glyco- and tauro-conjugated bile acids having a 7- or 12-oxo group have been synthesized. Introduction of a glucuronyl residue at the C-3 position was achieved by the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. The 3-glucuronides of conjugated bile acids were prepared by three sequential reactions : esterification with p-nitrophenol, glucuronidation at C-3, and amide formation with ethyl glycinate or taurine. The nuclear magnetic resonance spectral properties of 3-glucuronides of oxo bile acids and related compounds are briefly discussed.

  已合成具有7-或12-氧基团的未结合和糖结合、牛磺酸结合胆汁酸的3-葡萄糖醛酸酯。在C-3位引入葡萄糖醛酸残基是通过使用碳酸镉作为催化剂的Koenigs-Knorr反应实现的。结合胆汁酸的3-葡萄糖醛酸酯是通过三个串联反应制备的：与对硝基苯酚酯化、在C-3位进行葡萄糖醛酸化，以及与乙基甘氨酸或牛磺酸形成酰胺。简要讨论了氧基胆汁酸及相关化合物的3-葡萄糖醛酸酯的核磁共振光谱特性。
• NOVEL 7Beta-HYDROXYSTEROID DEHYDROGENASE MUTANTS AND PROCESS FOR THE PREPARATION OF URSODEOXYCHOLIC ACID
  申请人：Weuster-Botz Dirk

  公开号：US20140087421A1

  公开（公告）日：2014-03-27

  The invention relates to novel 7β-hydroxysteroid dehydrogenase mutants, to the sequences which encode these enzyme mutants, to processes for the preparation of the enzyme mutants and to their use in enzymatic reactions of cholic acid compounds, in particular in the preparation of ursodeoxycholic acid (UDCS). The invention also relates to novel processes for the synthesis of UDCS using the enzyme mutants; and to the preparation of UDCS using recombinant, multiply-modified microorganisms.

  本发明涉及新型7β-羟基类固醇脱氢酶突变体，编码这些酶突变体的序列，制备酶突变体的方法以及它们在胆酸化合物的酶促反应中的使用，特别是在制备熊去氧胆酸（UDCS）方面的使用。本发明还涉及使用这些酶突变体的新型UDCS合成方法；以及使用重组、多重修饰的微生物制备UDCS的方法。
• Novel 7beta-Hydroxysteroid Dehydrogenases and Their Use
  申请人：PharmaZell GmbH

  公开号：US20160194615A1

  公开（公告）日：2016-07-07

  The invention relates to novel 7β-hydroxysteroid dehydrogenases which are obtainable from bacteria of the genus Collinsella , especially of the strain Collinsella aerofaciens , to the sequences encoding said enzymes, to methods for producing said enzymes and to their use in the enzymatic conversion of cholic acid compounds, and especially in the production of ursodeoxycholic acid (UDCS). The invention also relates to novel methods for the synthesis UDCS.

  本发明涉及从Collinsella属的细菌中获得的新型7β-羟基类固醇脱氢酶，特别是从Collinsella aerofaciens菌株中获得的酶，以及编码该酶的序列，制备该酶的方法以及在胆酸化合物的酶转化中以及特别是在制备熊去氧胆酸（UDCS）中使用该酶。本发明还涉及UDCS的合成新方法。
• Synthesis of Gymnasterone B, an antitumor steroid from Gymnascella dankaliensis
  作者：Min Li、Peijie Zhou、Anmei Wu

  DOI：10.1016/j.tetlet.2006.03.072

  日期：2006.5

  A stereoselective approach toward a marine natural product, Gymnasterone B, has been achieved via a series reaction from cholic acid. (c) 2006 Elsevier Ltd. All rights reserved.
• Wieland; Kapitel, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1932, vol. 212, p. 269,273
  作者：Wieland、Kapitel

  DOI：——

  日期：——