(1R,9S,12R,13R,14E,17S,19S,20R,21S,23R)-13-ethyl-1-hydroxy-12-[[(2S,3S,4S)-4-hydroxy-5-[hydroxy-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]methyl]-3,5-dimethyloxolan-2-yl]methyl]-19,21-dimethoxy-15,17,23-trimethyl-11,24-dioxa-4-azatricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10-trione | 249268-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: (1R,9S,12R,13R,14E,17S,19S,20R,21S,23R)-13-ethyl-1-hydroxy-12-[[(2S,3S,4S)-4-hydroxy-5-[hydroxy-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]methyl]-3,5-dimethyloxolan-2-yl]methyl]-19,21-dimethoxy-15,17,23-trimethyl-11,24-dioxa-4-azatricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10-trione
• CAS: 249268-66-4
• 化学式: C₄₃H₇₁NO₁₃
• 分子量: 810.036
• InChiKey: HPZJNBIXVLCJAH-XAOFFINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1R,9S,12R,13R,14E,17S,19S,20R,21S,23R)-13-ethyl-1-hydroxy-12-[[(2S,3S,4S)-4-hydroxy-5-[hydroxy-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]methyl]-3,5-dimethyloxolan-2-yl]methyl]-19,21-dimethoxy-15,17,23-trimethyl-11,24-dioxa-4-azatricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10-trione 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 5.0h， 以83%的产率得到[(1R,2R,4R)-4-[acetyloxy-[(3S,4R,5S)-3-acetyloxy-5-[[(1R,9S,12R,13R,14E,17S,19S,20R,21S,23R)-13-ethyl-1-hydroxy-19,21-dimethoxy-15,17,23-trimethyl-2,3,10-trioxo-11,24-dioxa-4-azatricyclo[18.3.1.04,9]tetracos-14-en-12-yl]methyl]-2,4-dimethyloxolan-2-yl]methyl]-2-methoxycyclohexyl] acetate
  参考文献：
  名称：

  Ring Contraction of an Ascomycin Derivative to a 19-Membered Macrolactam

  摘要：

  Starting from readily available (22R)-26,33-bis-O-[(tert-butyl)dimethylsilyl]-22,22-O-dihydroisoascomycin (5), the synthesis of a doubly ring-contracted ascomycin derivative, the 19-membered macrolactam 10, is described.

  DOI：

  10.1002/(sici)1522-2675(19990707)82:7<1038::aid-hlca1038>3.0.co;2-i
• 作为产物：
  描述：

  (22R)-22,22-O-dihydroisoascomycin 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 148.5h， 生成 (1R,9S,12R,13R,14E,17S,19S,20R,21S,23R)-13-ethyl-1-hydroxy-12-[[(2S,3S,4S)-4-hydroxy-5-[hydroxy-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]methyl]-3,5-dimethyloxolan-2-yl]methyl]-19,21-dimethoxy-15,17,23-trimethyl-11,24-dioxa-4-azatricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10-trione
  参考文献：
  名称：

  Ring Contraction of an Ascomycin Derivative to a 19-Membered Macrolactam

  摘要：

  Starting from readily available (22R)-26,33-bis-O-[(tert-butyl)dimethylsilyl]-22,22-O-dihydroisoascomycin (5), the synthesis of a doubly ring-contracted ascomycin derivative, the 19-membered macrolactam 10, is described.

  DOI：

  10.1002/(sici)1522-2675(19990707)82:7<1038::aid-hlca1038>3.0.co;2-i