3α-hydroxy-7α,12α-diacetoxy-24-nor-5β-cholan-23-oic acid | 64743-81-3

• 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: 3α-hydroxy-7α,12α-diacetoxy-24-nor-5β-cholan-23-oic acid
• CAS: 64743-81-3
• 化学式: C₂₇H₄₂O₇
• 分子量: 478.626
• InChiKey: RTCCCNSSLSEIFS-ZEOHNGTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  110.13
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-7α,12α-diacetoxy-24-nor-5β-cholan-23-oic acid 在 palladium on activated charcoal 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 pentafluorophenyl 7α,12α-diacetoxy-3α-{N-[(tert-butoxy)carbonyl]-glycyl}-24-nor-5β-cholan-23-oate
  参考文献：
  名称：

  来自胆汁酸和甘氨酸的线性和环状二聚酯衍生物的合成

  摘要：

  摘要 从廉价的类固醇胆汁酸和氨基酸甘氨酸合成了两种新型泰勒制线性和环状二聚体。通过光谱分析确定所有中间体和二聚体的结构和立体化学。

  DOI：

  10.1081/scc-120015401
• 作为产物：
  描述：

  去甲胆酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 3α-hydroxy-7α,12α-diacetoxy-24-nor-5β-cholan-23-oic acid
  参考文献：
  名称：

  Synthesis of Cyclocholates and Derivatives

  摘要：

  A synthesis of bile acid cyclooligomers by the Yamaguchi method is described. Cyclotrimerization is the principal reaction route for the cholic acid system, and cyclotetramerization is the principal reaction route for the 24-norcholic acid.

  DOI：

  10.1080/00397919708004196

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。
• Dias,J.R.; Ramachandra,R., Synthetic Communications, 1977, vol. 7, p. 293 - 297
  作者：Dias,J.R.、Ramachandra,R.

  DOI：——

  日期：——
• Remarkable Structures of Cyclotri(deoxycholate) and Cyclotetra(24-norcholate) Acetate Esters
  作者：Jerry Ray Dias、Robert A. Pascal、Jason Morrill、Andrew J. Holder、Hongwu Gao、Charles Barnes

  DOI：10.1021/ja011797c

  日期：2002.5.1

  X-ray crystallographic determinations and AM1 calculations have defined the solid-state and gas-phase structures of cyclotri(deoxycholate) and cyclotetra(24-norcholate). The latter cyclotetramer is one of the largest open macrocycles ever subjected to crystallography.
• Synthesis of Cyclocholates and Derivatives
  作者：Hongwu Gao、Jerry Ray Dias

  DOI：10.1080/00397919708004196

  日期：1997.3

  A synthesis of bile acid cyclooligomers by the Yamaguchi method is described. Cyclotrimerization is the principal reaction route for the cholic acid system, and cyclotetramerization is the principal reaction route for the 24-norcholic acid.
• SYNTHESIS OF LINEAR AND CYCLIC DIMERIC ESTER DERIVATIVES FROM BILE ACIDS AND GLYCINE
  作者：Ze Tian、Hong Cui、Yan Wang

  DOI：10.1081/scc-120015401

  日期：2002.1.1

  ABSTRACT Two novel taylor-made linear and cyclic dimers were synthesized from the inexpensive steroid bile acids and amino acid glycine. The structures and stereochemistry of all intermediates and dimers were determined by means of spectroscopic analyses.

  摘要 从廉价的类固醇胆汁酸和氨基酸甘氨酸合成了两种新型泰勒制线性和环状二聚体。通过光谱分析确定所有中间体和二聚体的结构和立体化学。