benzyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxy-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 | 190326-36-4

• 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: benzyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxy-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: 190326-36-4
• 化学式: C₆₁H₉₈O₅Si
• 分子量: 939.532
• InChiKey: KLBAYIOBOOMFQY-ZWRIHFCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.18
• 重原子数：
  67
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxy-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 在 palladium on activated charcoal 氢氟酸 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
  参考文献：
  名称：

  Syntheses of Linear Dimeric and Cyclic Oligomeric Cholate Ester Derivatives

  摘要：

  利用 2-氯苯甲酰氯和 4-二甲氨基吡啶（DMAP）将石胆酸（1）环酯化，一步合成了石胆酸的环状三聚体 2 和四聚体 3。用类似的方法合成了 7,12-二乙酰基-24-去甲胆酸的四聚体 5（4）。这些结果表明，环三聚体是胆酸体系的首选循环尺寸，而环四聚体是 24-去甲胆酸体系的首选循环尺寸。石胆酸的环四聚体化比环二聚体化更可取。四聚体 3 的结构通过多步合成得到了验证。通过光谱分析确定了所有二聚体、低聚物和中间产物的结构和立体化学性质。

  DOI：

  10.1055/s-1997-1215
• 作为产物：
  描述：

  石胆酸 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 benzyl (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxy-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
  参考文献：
  名称：

  Syntheses of Linear Dimeric and Cyclic Oligomeric Cholate Ester Derivatives

  摘要：

  利用 2-氯苯甲酰氯和 4-二甲氨基吡啶（DMAP）将石胆酸（1）环酯化，一步合成了石胆酸的环状三聚体 2 和四聚体 3。用类似的方法合成了 7,12-二乙酰基-24-去甲胆酸的四聚体 5（4）。这些结果表明，环三聚体是胆酸体系的首选循环尺寸，而环四聚体是 24-去甲胆酸体系的首选循环尺寸。石胆酸的环四聚体化比环二聚体化更可取。四聚体 3 的结构通过多步合成得到了验证。通过光谱分析确定了所有二聚体、低聚物和中间产物的结构和立体化学性质。

  DOI：

  10.1055/s-1997-1215

文献信息

• Syntheses of Linear Dimeric and Cyclic Oligomeric Cholate Ester Derivatives
  作者：Yuexian Li、Jerry Ray Dias

  DOI：10.1055/s-1997-1215

  日期：1997.4

  One-step syntheses of cyclic trimer 2 and tetramer 3 of lithocholate were achieved from the cycloesterification of lithocholic acid (1) by using 2-chlorobenzoyl chloride and 4-dimethylaminopyridine (DMAP). The tetramer 5 of 7,12-diacetyl-24-norcholid acid (4) was synthesized by a similar method. These results suggest that the cyclotrimer is the preferred cycle size for the cholic acid system and that the cyclotetramer is the preferred cycle size for the 24-norcholic acid system. Cyclotetramerization of lithocholic acid is preferred over cyclodimerization. The structure of tetramer 3 was verified by a multistep synthesis. The structures and stereochemistry of all dimers, oligomers, and intermediate products were determined by means of spectroscopic analyses.

  利用 2-氯苯甲酰氯和 4-二甲氨基吡啶（DMAP）将石胆酸（1）环酯化，一步合成了石胆酸的环状三聚体 2 和四聚体 3。用类似的方法合成了 7,12-二乙酰基-24-去甲胆酸的四聚体 5（4）。这些结果表明，环三聚体是胆酸体系的首选循环尺寸，而环四聚体是 24-去甲胆酸体系的首选循环尺寸。石胆酸的环四聚体化比环二聚体化更可取。四聚体 3 的结构通过多步合成得到了验证。通过光谱分析确定了所有二聚体、低聚物和中间产物的结构和立体化学性质。