(1R,2R,3R,4S,5R,8R,9S,10S,11R,12R,14R)-11-[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-3,4-dihydroxy-9-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadecan-7-one | 225505-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3R,4S,5R,8R,9S,10S,11R,12R,14R)-11-[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-3,4-dihydroxy-9-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadecan-7-one
• CAS: 225505-03-3
• 化学式: C₃₅H₆₃NO₁₁
• 分子量: 673.885
• InChiKey: YVUFLFVRMPWWSX-KBONMUPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,4S,5R,8R,9S,10S,11R,12R,14R)-11-[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-3,4-dihydroxy-9-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadecan-7-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以80%的产率得到(1R,2R,3R,4S,5R,8R,9S,10S,11R,12R,14R)-5-ethyl-3,4-dihydroxy-11-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-piperidin-1-yloxan-2-yl]oxy-9-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadecan-7-one
  参考文献：
  名称：

  Synthesis of 8(R),9(R)-9-deoxo-4''-deoxy-6,9-epoxyerythromycin: potent motilides

  摘要：

  A series of new and potent motilides, 8(R),9(R)-9-deoxo-4 "-deoxy-6,9-epoxyerythromycin A was designed, synthesized and evaluated for gastrointestinal prokinetic activity. These compounds were acid-stable with many demonstrating in vitro potency markedly superior to erythromycin. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80059-2
• 作为产物：
  描述：

  4'-deoxyerythromycin A 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸酐 、 碘 、 sodium methylate 、 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 生成 (1R,2R,3R,4S,5R,8R,9S,10S,11R,12R,14R)-11-[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-3,4-dihydroxy-9-[(2S,4S,6S)-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadecan-7-one
  参考文献：
  名称：

  Synthesis of 8(R),9(R)-9-deoxo-4''-deoxy-6,9-epoxyerythromycin: potent motilides

  摘要：

  A series of new and potent motilides, 8(R),9(R)-9-deoxo-4 "-deoxy-6,9-epoxyerythromycin A was designed, synthesized and evaluated for gastrointestinal prokinetic activity. These compounds were acid-stable with many demonstrating in vitro potency markedly superior to erythromycin. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80059-2