(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylamino)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]pentanamide | 1189063-14-6

• 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: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylamino)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]pentanamide
• CAS: 1189063-14-6
• 化学式: C₅₈H₈₇N₃O₆
• 分子量: 922.345
• InChiKey: GKFIHKAXWMZGSI-CMRDRSECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  67
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  165
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylamino)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]pentanamide 、 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以38%的产率得到(4R)-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-[[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylamino)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-5-oxopentan-2-yl]-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-7,12-dihydroxy-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]amino]-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamide
  参考文献：
  名称：

  Spacer-Dependent Folding and Aggregation of Oligocholates in SDS Micelles

  摘要：

  Insertion of flexible, 4-aminobutyroyl spacers in between the cholate repeat units had been found previously to enhance the folding of cholate oligomers in homogeneous solution (Zhao, Y.J. Org. Chem. 2009, 74, 834-843). The opposite effect was observed when the oligomers were solubilized in aqueous solutions of sodium dodecyl Sulfate (SIDS), The spacers enabled Formation of tight aggregates of the oligocholates in SDS solutions when the surfactant was below its critical micelle concentration (CMC). Above the CMC, SDS micelles formed and dissociated the oligocholate aggregates. The parent oligocholates (without spacers in between the repeat units) also aggregated when they were too short to fold (e.g., dimer). The longer tetramer and hexamer preferred to fold, as their rigid, awkwardly shaped backbones prevented tight packing needed in the formation of stable aggregates. Folding was favored both below and above the CMC of SDS and was enhanced by an increase in the chain length.

  DOI：

  10.1021/jo901651h
• 作为产物：
  描述：

  (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylamino)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]pentanamide 在 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-5-(naphthalen-1-ylamino)-5-oxopentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]pentanamide
  参考文献：
  名称：

  Spacer-Dependent Folding and Aggregation of Oligocholates in SDS Micelles

  摘要：

  Insertion of flexible, 4-aminobutyroyl spacers in between the cholate repeat units had been found previously to enhance the folding of cholate oligomers in homogeneous solution (Zhao, Y.J. Org. Chem. 2009, 74, 834-843). The opposite effect was observed when the oligomers were solubilized in aqueous solutions of sodium dodecyl Sulfate (SIDS), The spacers enabled Formation of tight aggregates of the oligocholates in SDS solutions when the surfactant was below its critical micelle concentration (CMC). Above the CMC, SDS micelles formed and dissociated the oligocholate aggregates. The parent oligocholates (without spacers in between the repeat units) also aggregated when they were too short to fold (e.g., dimer). The longer tetramer and hexamer preferred to fold, as their rigid, awkwardly shaped backbones prevented tight packing needed in the formation of stable aggregates. Folding was favored both below and above the CMC of SDS and was enhanced by an increase in the chain length.

  DOI：

  10.1021/jo901651h