(3S,4S)-4-((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-N-methylbutanamido)-5-(tert-butoxy)-5-oxopent-1-en-3-yl palmitate | 1037307-73-5

• 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: (3S,4S)-4-((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-N-methylbutanamido)-5-(tert-butoxy)-5-oxopent-1-en-3-yl palmitate
• CAS: 1037307-73-5
• 化学式: C₅₃H₈₇N₃O₁₃
• 分子量: 974.286
• InChiKey: DWLIRENOYSQRMN-SWTKAGERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.98
• 重原子数：
  69.0
• 可旋转键数：
  30.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  186.49
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-N-methylbutanamido)-5-(tert-butoxy)-5-oxopent-1-en-3-yl palmitate 在 二甲基硫 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S)-3-((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-N-methylbutanamido)-4-(tert-butoxy)-1,4-dioxobutan-2-yl palmitate
  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：

  N-[(1S,2S)-1-tert-butoxycarbonyl-2-hydroxy-3-butenyl]-N-methyl-2-benzyloxycarbonylamino-3-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-2-hydroxybutanamide 、 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 24.0h， 生成 (3S,4S)-4-((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4R,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-N-methylbutanamido)-5-(tert-butoxy)-5-oxopent-1-en-3-yl palmitate
  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