21,23-Di-O-methylconcanolide A | 147344-95-4

• 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: 21,23-Di-O-methylconcanolide A
• CAS: 147344-95-4
• 化学式: C₄₁H₆₈O₁₀
• 分子量: 720.985
• InChiKey: ODAYTYKLLZJIMR-SWTZZOJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  51.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  133.14
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  21,23-Di-O-methylconcanolide A 在 水 、 三氯化铁 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以90%的产率得到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
• 作为产物：
  描述：

  甲醇 、 刀豆素 C 在 对甲苯磺酸 作用下， 反应 3.0h， 以89%的产率得到21,23-Di-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