Tert-butyl 2-[2-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-oxoethyl]-2-hydroxy-4-[5-[(4-methoxy-4-oxobutanoyl)-phenylmethoxyamino]pentylamino]-4-oxobutanoate | 153492-20-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Tert-butyl 2-[2-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-oxoethyl]-2-hydroxy-4-[5-[(4-methoxy-4-oxobutanoyl)-phenylmethoxyamino]pentylamino]-4-oxobutanoate
• CAS: 153492-20-7
• 化学式: C₄₁H₆₀N₄O₁₁
• 分子量: 784.948
• InChiKey: AKOIGDAICVUNFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  56
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  190
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[2-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-oxoethyl]-2-hydroxy-4-[5-[(4-methoxy-4-oxobutanoyl)-phenylmethoxyamino]pentylamino]-4-oxobutanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems

  摘要：

  The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.

  DOI：

  10.1021/jo00079a007
• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-1-戊醇 在 吡啶 、 potassium dihydrogenphosphate 、 三苯基膦 、 三氟乙酸 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 31.5h， 生成 Tert-butyl 2-[2-[5-[acetyl(phenylmethoxy)amino]pentylamino]-2-oxoethyl]-2-hydroxy-4-[5-[(4-methoxy-4-oxobutanoyl)-phenylmethoxyamino]pentylamino]-4-oxobutanoate
  参考文献：
  名称：

  Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems

  摘要：

  The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.

  DOI：

  10.1021/jo00079a007