2-Hydroxy-1,2,3-propanetricarboxylic acid 2-tert-butyl 1,3-bis(p-nitrophenyl) triester | 153492-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-Hydroxy-1,2,3-propanetricarboxylic acid 2-tert-butyl 1,3-bis(p-nitrophenyl) triester
• 英文别名: 2-O-tert-butyl 1-O,3-O-bis(4-nitrophenyl) 2-hydroxypropane-1,2,3-tricarboxylate
• CAS: 153492-04-7
• 化学式: C₂₂H₂₂N₂O₁₁
• 分子量: 490.423
• InChiKey: HDTCDXAJFHYDFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  191
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-1,2,3-propanetricarboxylic acid 2-tert-butyl 1,3-bis(p-nitrophenyl) triester 以 氯仿 、 乙腈 为溶剂， 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
• 作为产物：
  描述：

  tert-butyl-1,5-dimethyl citrate 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.5h， 生成 2-Hydroxy-1,2,3-propanetricarboxylic acid 2-tert-butyl 1,3-bis(p-nitrophenyl) triester
  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

文献信息

• Total synthesis and structure revision of petrobactin
  作者：Raymond J Bergeron、Guangfei Huang、Richard E Smith、Neelam Bharti、James S McManis、Alison Butler

  DOI：10.1016/s0040-4020(03)00103-0

  日期：2003.3

  The total synthesis and the revised structural assignment of petrobactin, a siderophore isolated from the marine bacterium Marinobacter hydrocarbonoclasticus, is reported. The key step in the synthesis involved condensation of N1-(2,3-dibenzoyloxybenzoyl)-N4-benzylspermidine with 1,3-di-(p-nitrophenyl)-2-tert-butyl citrate. Proton NMR spectra of the synthesized product compared with those reported

  总合成和petrobactin订正结构分配，从所述海洋细菌中分离的铁载体Marinobacter hydrocarbonoclasticus，报道。在合成参与缩合的关键步骤Ñ 1 - （2,3- dibenzoyloxybenzoyl） - ñ 4 -benzylspermidine与1,3-二- （p -硝基苯基）-2-叔柠檬酸丁酯。合成产物的质子NMR谱与报道的天然产物相比，表明该化合物不含已公开的2，3-二羟基苯甲酰基。相反，分裂模式表明存在3，4-二羟基苯甲酰基片段。3，4-二羟基苯甲酰基类似物是通过类似的途径获得的。该化合物的质子和碳13 NMR谱图与报道的天然岩蛋白相似。
• Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems
  作者：Arun Ghosh、Marvin J. Miller

  DOI：10.1021/jo00079a007

  日期：1993.12

  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.