tert-butyl (2S,5S,6S)-2-((S)-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)((triethylsilyl)oxy)methyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate | 1037307-67-7

• 分子结构分类: 有机化合物
• 英文名称: tert-butyl (2S,5S,6S)-2-((S)-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)((triethylsilyl)oxy)methyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate
• CAS: 1037307-67-7
• 化学式: C₄₆H₈₀N₄O₁₁Si
• 分子量: 893.247
• InChiKey: UBZKSAJMVSDWNG-DNYMQCIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  62.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  167.93
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5S,6S)-2-((S)-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)((triethylsilyl)oxy)methyl)-1,4-dimethyl-3-oxo-6-(palmitoyloxy)-1,4-diazepane-5-carboxylate 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.0h， 以100%的产率得到C₃₃H₅₄N₄O₁₁
  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：

  tert-butyl (2S,5S,6S)-2-((S)-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)((triethylsilyl)oxy)methyl)-6-hydroxy-1,4-dimethyl-3-oxo-1,4-diazepane-5-carboxylate 、 棕榈酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以81%的产率得到tert-butyl (2S,5S,6S)-2-((S)-((3aR,4S,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)((triethylsilyl)oxy)methyl)-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