2',11-diacetyl-4''-O-<(methoxycarbonyl)sulfamoyl>oleandomycin | 66065-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',11-diacetyl-4''-O-<(methoxycarbonyl)sulfamoyl>oleandomycin
• 英文别名: 2',11-diacetyl-4"-O-<(methoxycarbonyl)sulfamoyl>oleandomycin；2',11-diacetyl-4"-O-[(methoxycarbonyl)sulfamoyl]oleandomycin
• CAS: 66065-98-3
• 化学式: C₄₁H₆₈N₂O₁₈S
• 分子量: 909.06
• InChiKey: NSKACZVFQCQSMN-BLINGQLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  62.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  239.59
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2',11-diacetyl-4''-O-<(methoxycarbonyl)sulfamoyl>oleandomycin 在 甲醇 作用下， 以 xylene 为溶剂， 反应 49.5h， 生成 11-acetyl-3-O-(3"-methoxy-4"-vinylfuranosyl)oleandomycin
  参考文献：
  名称：

  Ring contraction of oleandrose on the macrolide antibiotic oleandomycin with [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt

  摘要：

  Ring contraction of the neutral oleandrose sugar in the 14-membered-ring macrolide antibiotic oleandomycin (2) has been accomplished using [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt (1). The product of this interesting rearrangement, after methanolic hydrolysis of the 2'-acetate, is the 11-acetyl-3-O-(3"-methoxy-4"-vinylfuranosyl)oleandomycin (12). The in vitro activity of furanoside 12 is only moderately less than that of 11-acetyloleandomycin (13).

  DOI：

  10.1021/jm00349a025
• 作为产物：
  描述：

  伯吉斯试剂 、 2',11-diacetyloleandomycin 以 苯 为溶剂， 反应 20.0h， 以0.4 g的产率得到2',11-diacetyl-4''-O-<(methoxycarbonyl)sulfamoyl>oleandomycin
  参考文献：
  名称：

  Ring contraction of oleandrose on the macrolide antibiotic oleandomycin with [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt

  摘要：

  Ring contraction of the neutral oleandrose sugar in the 14-membered-ring macrolide antibiotic oleandomycin (2) has been accomplished using [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt (1). The product of this interesting rearrangement, after methanolic hydrolysis of the 2'-acetate, is the 11-acetyl-3-O-(3"-methoxy-4"-vinylfuranosyl)oleandomycin (12). The in vitro activity of furanoside 12 is only moderately less than that of 11-acetyloleandomycin (13).

  DOI：

  10.1021/jm00349a025