tert-butyl (2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-((methyl)(2,2,2-trichloroethoxycarbonyl)amino)-4-pentenoate | 1004751-04-5

• 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: tert-butyl (2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-((methyl)(2,2,2-trichloroethoxycarbonyl)amino)-4-pentenoate
• 英文别名: tert-butyl (2S,3S)-3-[tert-butyl(diphenyl)silyl]oxy-2-[methyl(2,2,2-trichloroethoxycarbonyl)amino]pent-4-enoate
• CAS: 1004751-04-5
• 化学式: C₂₉H₃₈Cl₃NO₅Si
• 分子量: 615.069
• InChiKey: BGRYOTPQGQRTFB-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-((methyl)(2,2,2-trichloroethoxycarbonyl)amino)-4-pentenoate 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以91%的产率得到tert-butyl (2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-(methylamino)-4-pentenoate
  参考文献：
  名称：

  Synthesis of Caprazamycin Analogues and Their Structure−Activity Relationship for Antibacterial Activity

  摘要：

  Synthesis of palmitoyl caprazol 7, which possesses a simple fatty acyl side chain at the 3"'-position of the diazepanone moiety, was carried out and their antibacterial activity was evaluated. The key elements of our approach include the improved synthesis of the key 5'-p-0-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive amination. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 mu g/mL) with potency similar to that of the caprazamycins (CPZs). Palmitoyl caprazol 7 and N-6'-desmethyl palmitoyl caprazol 28 also exhibited antibacterial activity against drug-resistant bacteria including methyciline-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE) strains (MIC = 3.13-12.5 mu g/mL).

  DOI：

  10.1021/jo702264e
• 作为产物：
  描述：

  (2S,3S)-3-[tert-butyl(diphenyl)silyl]oxy-2-[methyl(2,2,2-trichloroethoxycarbonyl)amino]pent-4-enoic acid 、 叔丁基三氯乙酰亚胺酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以47 mg的产率得到tert-butyl (2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-((methyl)(2,2,2-trichloroethoxycarbonyl)amino)-4-pentenoate
  参考文献：
  名称：

  Synthesis of Caprazamycin Analogues and Their Structure−Activity Relationship for Antibacterial Activity

  摘要：

  Synthesis of palmitoyl caprazol 7, which possesses a simple fatty acyl side chain at the 3"'-position of the diazepanone moiety, was carried out and their antibacterial activity was evaluated. The key elements of our approach include the improved synthesis of the key 5'-p-0-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive amination. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 mu g/mL) with potency similar to that of the caprazamycins (CPZs). Palmitoyl caprazol 7 and N-6'-desmethyl palmitoyl caprazol 28 also exhibited antibacterial activity against drug-resistant bacteria including methyciline-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE) strains (MIC = 3.13-12.5 mu g/mL).

  DOI：

  10.1021/jo702264e

文献信息

• Synthesis of Caprazamycin Analogues and Their Structure−Activity Relationship for Antibacterial Activity
  作者：Shinpei Hirano、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1021/jo702264e

  日期：2008.1.1

  Synthesis of palmitoyl caprazol 7, which possesses a simple fatty acyl side chain at the 3"'-position of the diazepanone moiety, was carried out and their antibacterial activity was evaluated. The key elements of our approach include the improved synthesis of the key 5'-p-0-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive amination. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 mu g/mL) with potency similar to that of the caprazamycins (CPZs). Palmitoyl caprazol 7 and N-6'-desmethyl palmitoyl caprazol 28 also exhibited antibacterial activity against drug-resistant bacteria including methyciline-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE) strains (MIC = 3.13-12.5 mu g/mL).