methyl (3α,5α,12α)-3-hydroxy-12-methoxymethyloxy-cholan-24-oate | 1319714-63-0

• 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: methyl (3α,5α,12α)-3-hydroxy-12-methoxymethyloxy-cholan-24-oate
• 英文别名: methyl (4R)-4-[(3R,5S,8R,9S,10S,12S,13R,14S,17R)-3-hydroxy-12-(methoxymethoxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1319714-63-0
• 化学式: C₂₇H₄₆O₅
• 分子量: 450.659
• InChiKey: VRBCGYYEZPIJFK-GJZUCAABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3α,5α,12α)-3-hydroxy-12-methoxymethyloxy-cholan-24-oate 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以93%的产率得到(3alpha,5alpha,12alpha)-3,12-二羟基胆烷-24-酸
  参考文献：
  名称：

  A stereoselective synthesis of the allo-bile acids from the 5β-isomers

  摘要：

  The allo-bile acids are a subset of the family of steroidal detergents found in most vertebrates. Because there are no major biological feedstocks for isolation of the alto-bile acids, they must be synthesized from the abundant 5 beta-reduced isomers. Here we report a general set of methods for the synthesis of allo-bile acids from the corresponding 5-beta isomers demarcated by a selective C-3 oxidation, IBX unsaturation, and stereoselective saturation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.140
• 作为产物：
  描述：

  脱氧胆酸甲酯 在 2-iodoxybenzoic acid 、 四磷十氧化物 、 氨 、 lithium 、 potassium tri-sec-butyl-borohydride 、 叔丁醇 作用下， 以 四氢呋喃 、 氯仿 、 二甲基亚砜 、 甲苯 为溶剂， 反应 78.08h， 生成 methyl (3α,5α,12α)-3-hydroxy-12-methoxymethyloxy-cholan-24-oate
  参考文献：
  名称：

  A stereoselective synthesis of the allo-bile acids from the 5β-isomers

  摘要：

  The allo-bile acids are a subset of the family of steroidal detergents found in most vertebrates. Because there are no major biological feedstocks for isolation of the alto-bile acids, they must be synthesized from the abundant 5 beta-reduced isomers. Here we report a general set of methods for the synthesis of allo-bile acids from the corresponding 5-beta isomers demarcated by a selective C-3 oxidation, IBX unsaturation, and stereoselective saturation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.140

文献信息

• A stereoselective synthesis of the allo-bile acids from the 5β-isomers
  作者：Qingjiang Li、Gregory P. Tochtrop

  DOI：10.1016/j.tetlet.2011.05.140

  日期：2011.8

  The allo-bile acids are a subset of the family of steroidal detergents found in most vertebrates. Because there are no major biological feedstocks for isolation of the alto-bile acids, they must be synthesized from the abundant 5 beta-reduced isomers. Here we report a general set of methods for the synthesis of allo-bile acids from the corresponding 5-beta isomers demarcated by a selective C-3 oxidation, IBX unsaturation, and stereoselective saturation. (C) 2011 Elsevier Ltd. All rights reserved.