N-[(1S,2S)-1-tert-butoxycarbonyl-2-hydroxy-3-butenyl]-N-methyl-6-benzyloxycarbonylamino-5-O-triethylsilyl-6-deoxy-2,3-O-isopropylidene-1-(uracil-1-yl)-β-D-glycelo-L-talo-heptofuranuronamide | 1037307-60-0

• 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: N-[(1S,2S)-1-tert-butoxycarbonyl-2-hydroxy-3-butenyl]-N-methyl-6-benzyloxycarbonylamino-5-O-triethylsilyl-6-deoxy-2,3-O-isopropylidene-1-(uracil-1-yl)-β-D-glycelo-L-talo-heptofuranuronamide
• CAS: 1037307-60-0
• 化学式: C₃₂H₄₂N₄O₁₂
• 分子量: 674.705
• InChiKey: MTRQDGQCTNBNRY-PUVAMVDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  207.95
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S)-1-tert-butoxycarbonyl-2-hydroxy-3-butenyl]-N-methyl-6-benzyloxycarbonylamino-5-O-triethylsilyl-6-deoxy-2,3-O-isopropylidene-1-(uracil-1-yl)-β-D-glycelo-L-talo-heptofuranuronamide 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  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,3S)-3-(tert-butyldiphenylsilyloxy)-2-(methylamino)-4-pentenoate 、 在 碳酸氢钠 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 186.0h， 以106 mg的产率得到N-[(1S,2S)-1-tert-butoxycarbonyl-2-hydroxy-3-butenyl]-N-methyl-6-benzyloxycarbonylamino-5-O-triethylsilyl-6-deoxy-2,3-O-isopropylidene-1-(uracil-1-yl)-β-D-glycelo-L-talo-heptofuranuronamide
  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