(1S,2R,5S,7R,9R,10S,12R,14R,15S,19S)-19-ethyl-7,15-dihydroxy-14-methyl-20-oxatetracyclo[10.10.0.02,10.05,9]docos-3-ene-13,21-dione | 1027219-24-4

• 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: (1S,2R,5S,7R,9R,10S,12R,14R,15S,19S)-19-ethyl-7,15-dihydroxy-14-methyl-20-oxatetracyclo[10.10.0.02,10.05,9]docos-3-ene-13,21-dione
• CAS: 1027219-24-4
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: DUYBJSUUORQMHP-DFJUZVJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (1S,2R,5S,7R,9R,10S,12R,14R,15S,19S)-19-ethyl-7,15-dihydroxy-14-methyl-20-oxatetracyclo[10.10.0.02,10.05,9]docos-3-ene-13,21-dione 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 of 13,14β-Dihydro A83543A aglycon 9α-O-TBDMS ether
  参考文献：
  名称：

  Chemistry of A83543A Derivatives. 1. Oxidations and Reductions of A83543A Aglycon

  摘要：

  A retro-biomimetic degradation of the A83543 tetracyclic ring system was investigated as one approach to obtaining putative polyketide-derived, late-stage biosynthetic precursors for the subsequent study of their cyclizations. However, initial studies revealed an unexpected chemical stability of the ring system that required the development of indirect methods to cleave the ring-forming bonds. Hydride reagents were especially useful for reductively cleaving the lactone and generating novel derivatives, whose structures and stereochemistries were determined by detailed NMR analyses correlated with results from molecular modeling. The latter were also used to rationalize the conformational behaviors and lack of reactivities exhibited by the macrocyclic lactone systems in the parent and 13,14-enone-reduced derivatives.

  DOI：

  10.1021/jo00085a049
• 作为产物：
  描述：

  多杀菌素 在 吡啶 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.5h， 生成 (1S,2R,5S,7R,9R,10S,12R,14R,15S,19S)-19-ethyl-7,15-dihydroxy-14-methyl-20-oxatetracyclo[10.10.0.02,10.05,9]docos-3-ene-13,21-dione
  参考文献：
  名称：

  Chemistry of A83543A Derivatives. 1. Oxidations and Reductions of A83543A Aglycon

  摘要：

  A retro-biomimetic degradation of the A83543 tetracyclic ring system was investigated as one approach to obtaining putative polyketide-derived, late-stage biosynthetic precursors for the subsequent study of their cyclizations. However, initial studies revealed an unexpected chemical stability of the ring system that required the development of indirect methods to cleave the ring-forming bonds. Hydride reagents were especially useful for reductively cleaving the lactone and generating novel derivatives, whose structures and stereochemistries were determined by detailed NMR analyses correlated with results from molecular modeling. The latter were also used to rationalize the conformational behaviors and lack of reactivities exhibited by the macrocyclic lactone systems in the parent and 13,14-enone-reduced derivatives.

  DOI：

  10.1021/jo00085a049