sodium;2-[(2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(1S,2S,4R)-1,5-dihydroxy-2,4,5-trimethylhexyl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-5-methoxy-4-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-3-methyloxan-2-yl]acetate | 140901-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium;2-[(2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(1S,2S,4R)-1,5-dihydroxy-2,4,5-trimethylhexyl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-5-methoxy-4-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-3-methyloxan-2-yl]acetate
• CAS: 140901-41-3
• 化学式: C₅₃H₉₁O₁₈*Na
• 分子量: 1039.28
• InChiKey: IJBMLHJQEPKNLZ-WZCNIXCNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  72
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  232
• 氢给体数：
  4
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  甲基溴化镁 、 sodium;2-[(2R,3S,4S,5R,6S)-2-hydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-4-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-3-methyloxan-2-yl]acetate 以 乙醚 为溶剂， 反应 1.0h， 以30%的产率得到sodium;2-[(2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(1S,2S,4R)-1,5-dihydroxy-2,4,5-trimethylhexyl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-5-methoxy-4-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-3-methyloxan-2-yl]acetate
  参考文献：
  名称：

  Synthetic modification of a novel microbial ionophore: exploration of anticoccidial structure-activity relationships

  摘要：

  While fermentation-derived polyether ionophores such as salinomycin are the dominant class of anticoccidial feed additives, there is little information concerning the structural features which confer optimal potency/efficacy in this important series. The recently discovered microbial polyether 1a, featuring potent, broad-spectrum anticoccidial activity, was employed as a template to explore structure-activity relationships. A number of single-step synthetic modifications targeted structural changes in both the lipophilic carbon backbone and the ion-binding cavity of 1a. Although previous semisynthetic transformations among the polyether ionophores almost always resulted in a substantial loss of anticoccidial activity, we obtained several analogues, altered on the periphery of the ionophore-ion complex, which retain good potency and efficacy. Monoglycone 7 (semduramicin sodium) has the most impressive anticoccidial profile of this series, and is undergoing further biological testing under field conditions.

  DOI：

  10.1021/jm00088a020