23-O-Methylconcanolide A | 147344-94-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 23-O-Methylconcanolide A
• CAS: 147344-94-3
• 化学式: C₄₀H₆₆O₁₀
• 分子量: 706.958
• InChiKey: XXUZOBJKLZYMQK-CMXLEQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  144.14
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  23-O-Methylconcanolide A 在 吡啶 、 水 、 三氯化铁 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 9,23-Di-O-Acetylconcanolide A
  参考文献：
  名称：

  Chemistry of unusual macrolides. 1. Preparation of the aglycons of concanamycin A and elaiophylin

  摘要：

  The aglycons of the concanamycins (1, 2) and elaiophylin (11) have been prepared for direct comparison to the vacuolar-type ATPase inhibitor bafilomycin A1 (10). The deglycosylation was achieved by acid hydrolysis in the absence of MeOH, while acid-catalyzed methanolysis proceed ed with unexpected displacement of carbohydrate residues rather than methoxy groups. Structure assignments of the derivatives were made with the help of one- and two-dimensional NMR studies. Especially helpful were the 9-O-acetylated concanamycin derivatives because they showed reduced flexibility of the macrolactone ring. As a result of a detailed analysis of the O-methyl derivatives of elaiolide (15) the structure of an earlier reported aglycon derivative of elaiophylin has to be revised to 12.

  DOI：

  10.1021/jo00072a036
• 作为产物：
  描述：

  刀豆素 C 在 水 、 三氯化铁 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 3.17h， 生成 23-O-Methylconcanolide A
  参考文献：
  名称：

  Chemistry of unusual macrolides. 1. Preparation of the aglycons of concanamycin A and elaiophylin

  摘要：

  The aglycons of the concanamycins (1, 2) and elaiophylin (11) have been prepared for direct comparison to the vacuolar-type ATPase inhibitor bafilomycin A1 (10). The deglycosylation was achieved by acid hydrolysis in the absence of MeOH, while acid-catalyzed methanolysis proceed ed with unexpected displacement of carbohydrate residues rather than methoxy groups. Structure assignments of the derivatives were made with the help of one- and two-dimensional NMR studies. Especially helpful were the 9-O-acetylated concanamycin derivatives because they showed reduced flexibility of the macrolactone ring. As a result of a detailed analysis of the O-methyl derivatives of elaiolide (15) the structure of an earlier reported aglycon derivative of elaiophylin has to be revised to 12.

  DOI：

  10.1021/jo00072a036