tert-butyl (2S,5S,6S)-2-((R)-1-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)ethyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate | 1037307-76-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S,5S,6S)-2-((R)-1-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)ethyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate
• CAS: 1037307-76-8
• 化学式: C₄₅H₈₁N₃O₁₁
• 分子量: 840.152
• InChiKey: PGZCEJOLATWHBT-GCVPECGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  59.0
• 可旋转键数：
  23.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  151.4
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5S,6S)-2-((R)-1-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)ethyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate 、 三氟乙酸 以 水 为溶剂， 反应 24.0h， 以100%的产率得到(2S,5S,6S)-2-((R)-1-(((2R,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)ethyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylic acid compound with 2,2,2-trifluoroacetic acid (1:1)
  参考文献：
  名称：

  Structure–activity relationship of truncated analogs of caprazamycins as potential anti-tuberculosis agents

  摘要：

  Systematic structure-activity relationship studies of caprazamycin (CPZ) analogs, including the aminoribose-truncated 5 and the uridine-truncated 6, have been carried out. Both 5 and 6 were synthesized efficiently via diazepanone ring construction by intramolecular reductive alkylation of aminoaldehyde derivatives. The antibacterial activity of a range of analogs, including 5 and 6, against Mycobacteriumosis was evaluated, and it was found that the uridine, the aminoribose, and the fatty acyl side chains are crucial for antibacterial activity. This study would be a guide for designing novel anti-tuberculosis agents based on the 6'-N-alkyl-5'-beta-O-aminoribosyl-glycyluridine class of antibiotics including the CPZs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.020
• 作为产物：
  描述：

  聚合甲醛 、 tert-butyl (2S,5S,6S)-2-((R)-1-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)ethyl)-4-methyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 72.0h， 以82%的产率得到tert-butyl (2S,5S,6S)-2-((R)-1-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)ethyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate
  参考文献：
  名称：

  Structure–activity relationship of truncated analogs of caprazamycins as potential anti-tuberculosis agents

  摘要：

  Systematic structure-activity relationship studies of caprazamycin (CPZ) analogs, including the aminoribose-truncated 5 and the uridine-truncated 6, have been carried out. Both 5 and 6 were synthesized efficiently via diazepanone ring construction by intramolecular reductive alkylation of aminoaldehyde derivatives. The antibacterial activity of a range of analogs, including 5 and 6, against Mycobacteriumosis was evaluated, and it was found that the uridine, the aminoribose, and the fatty acyl side chains are crucial for antibacterial activity. This study would be a guide for designing novel anti-tuberculosis agents based on the 6'-N-alkyl-5'-beta-O-aminoribosyl-glycyluridine class of antibiotics including the CPZs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.020