12,13-epoxydesmycosin | 90136-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12,13-epoxydesmycosin
• CAS: 90136-00-8
• 化学式: C₃₉H₆₅NO₁₅
• 分子量: 787.943
• InChiKey: IHFQPYBTKOWAKT-LHILHLNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  55.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  212.51
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (3S,5R)-3,5-dimethylpiperidine 、 12,13-epoxydesmycosin 在 sodium cyanoborohydride 作用下， 生成 12,13-epoxytilmicosin
  参考文献：
  名称：

  Identification and Synthesis of an Oxidation Product of Tilmicosin

  摘要：

  During formulation development of the veterinary macrolide antibiotic tilmicosin, an oxidation product of the parent molecule was identified. Use of liquid chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy characterized the structure as 12,13-epoxytilmicosin, resulting from the oxidation of the double bond at the 12,13-position of the macrolide dienone. The synthesis of this oxidation product for confirmation of structural identity is described. The synthetic compound was identical to the isolated oxidation product, 12,13-epoxytilmicosin.

  DOI：

  10.1021/jf9710746
• 作为产物：
  描述：

  desmycosin-20-diethylketal 在 三仲丁基硼烷 、 硫酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 3.0h， 生成 12,13-epoxydesmycosin
  参考文献：
  名称：

  Identification and Synthesis of an Oxidation Product of Tilmicosin

  摘要：

  During formulation development of the veterinary macrolide antibiotic tilmicosin, an oxidation product of the parent molecule was identified. Use of liquid chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy characterized the structure as 12,13-epoxytilmicosin, resulting from the oxidation of the double bond at the 12,13-position of the macrolide dienone. The synthesis of this oxidation product for confirmation of structural identity is described. The synthetic compound was identical to the isolated oxidation product, 12,13-epoxytilmicosin.

  DOI：

  10.1021/jf9710746

文献信息

• Semisynthetic macrolide antibacterials derived from tylosin. Synthesis of 3-O-acetyl-23-O-demycinosyl-4″-O-isovaleryltylosin and related compounds, as well as the 12,13-epoxy derivatives
  作者：Andrew G. Fishman、Alan K. Mallams、Randall R. Rossman

  DOI：10.1039/p19890000787

  日期：——

  syntheses of the 2′-O-acetyl, 23-O-acetyl, and 2′,23-di-O-acetyl derivatives of the latter are also described. The synthesis of key hydrazones is also described. The regio- and stereo-selective epoxidation of tylosin and its acyl derivatives afforded the 12,13-epoxy analogues, which were used to synthesize novel acylated 12,13-epoxy derivatives of 23-O-demycinosyltylosin.

  已经开发出选择性的酰化技术，其使得能够以有效的方式合成3 - O-乙酰基-4” -O-异戊基酪氨醇和3 - O-乙酰基-23- O-去甲霉素-4” -O-异戊基酪氨素。从泰乐菌素开始。还描述了后者的2'- O-乙酰基，23- O-乙酰基和2'，23-二-O-乙酰基衍生物的合成。还描述了关键的合成。泰乐菌素及其酰基衍生物的区域和立体选择性环氧化提供了12,13-环氧类似物，其被用于合成新型的23- O-脱mycinosyltylosin的酰化的12,13-环氧衍生物。