p-bromophenacyl (24R,25R)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate | 116382-78-6

• 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: p-bromophenacyl (24R,25R)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate
• 英文别名: [2-(4-bromophenyl)-2-oxoethyl] (2R,3R,6R)-3-hydroxy-2-methyl-6-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoate
• CAS: 116382-78-6
• 化学式: C₃₅H₅₁BrO₇
• 分子量: 663.69
• InChiKey: ONQKWBOGYQARIA-LXDONRFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-bromophenacyl (24R,25R)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate 生成 (2R,3R,6R)-3-hydroxy-2-methyl-6-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-4,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid
  参考文献：
  名称：

  KINOSHITA, TAKUMI;MIYATA, MASAAKI;ISMAIL, SHAHNAZ M.;FUJIMOTO, YOSHINORI;+, CHEM. AND PHARM. BULL., 36,(1988) N 1, 134-141

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R,6R)-3-hydroxy-2-methyl-6-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-4,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid 、 2,4'-二溴苯乙酮 生成 p-bromophenacyl (24R,25R)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-26-oate
  参考文献：
  名称：

  KINOSHITA, TAKUMI;MIYATA, MASAAKI;ISMAIL, SHAHNAZ M.;FUJIMOTO, YOSHINORI;+, CHEM. AND PHARM. BULL., 36,(1988) N 1, 134-141

  摘要：

  DOI：

文献信息

• Synthesis and determination of stereochemistry of four diastereoisomers at the C-24 and C-25 positions of 3.ALPHA.,7.ALPHA.,12.ALPHA.,24-tetrahydroxy-5.BETA.-cholestan-26-oic acid.
  作者：TAKUMI KINOSHITA、MASAAKI MIYATA、SHAHNAZ M. ISMAIL、YOSHINORI FUJIMOTO、KATSHMI KAKINUMA、NOBUO IKEKAWA、MASUO MORISAKI

  DOI：10.1248/cpb.36.134

  日期：——

  Four diastereoisomers at the C-24 and C-25 positions of 3α, 7α, 12α, 24-tetrahydroxy-5β-cholestan-26-oic acid (varanic acid) were synthesized in a stereochemically defined manner and also by a non-stereoselective route, followed by chromatographic separation. Their stereochemistry at the C-24 and C-25 positions was established on the basis of the known stereochemical course of the reactions employed for the synthesis, and 1H and 13C-nuclear magnetic resonance spectroscopic data of these isomers. It is concluded from the present work that the previous stereochemical assignment for the (24R, 25S) and (24R, 25R) isomers must be revised.

  在C-24和C-25位点合成了四个3α, 7α, 12α, 24-四羟基-5β-胆烷-26-酸（varanic acid）的立体异构体，既采用了立体化学定义的方法，也通过非立体选择性路线，然后进行色谱分离。根据用于合成的反应已知的立体化学过程以及这些异构体的1H和13C核磁共振光谱数据，确定了它们在C-24和C-25位点的立体化学。本研究得出的结论是，之前对（24R，25S）和（24R，25R）异构体的立体化学分配必须进行修正。