3-[(2R,4S)-1-tert-Butoxycarbonyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-pentanedioic acid diethyl ester | 442681-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-[(2R,4S)-1-tert-Butoxycarbonyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-pentanedioic acid diethyl ester
• CAS: 442681-36-9
• 化学式: C₂₄H₄₅NO₇Si
• 分子量: 487.709
• InChiKey: RBDATNQBVBOFPP-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-[(2R,4S)-1-tert-Butoxycarbonyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-pentanedioic acid diethyl ester 在 lithium aluminium tetrahydride 、 三甲基膦 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 13.5h， 生成 (2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyano-4-phenylsulfonylcyclohexyl)pyrrolidine
  参考文献：
  名称：

  Structure–Activity Relationships of 1β-Methyl-2-(5-phenylpyrrolidin-3-ylthio)carbapenems

  摘要：

  Structure-activity relationship studies of 1beta-methyl-2-[(3S,5R)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio]carbapenems, especially those pertaining to the relationship between antibacterial activity and side-chain structure were conducted. These studies suggested that the trans-(3S,5R)-5-phenylpyrrolidin-3-ylthio side-chain and the aminomethyl group at the 4-position of the phenyl ring play a key role in enhancing the antibacterial activity against the MRSA and Pseudomonas aeruginosa strains. In particular, the basicity of a substituent at the 4-position of the phenyl ring were shown to greatly contribute to the antibacterial activity against MRSA and methicillin-resistant Staphlyloccocus epidermidis strains. In contrast, the amidine group was shown to lead to potent antibacterial activity against P. aeruginosa strains comparable to that of imipenem, however, a good correlation between the basicity of the 4-substituent and antipseudomonal activity was not observed. In conclusion, the 4-aminomethyl or methylaminomethyl group on the phenyl ring was the best substituent for antipseudomonal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00430-8
• 作为产物：
  描述：

  (2R,4R)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-formyl-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 在 咪唑 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 三苯基膦 、 sodium chloride 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.84h， 生成 3-[(2R,4S)-1-tert-Butoxycarbonyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-pentanedioic acid diethyl ester
  参考文献：
  名称：

  Structure–Activity Relationships of 1β-Methyl-2-(5-phenylpyrrolidin-3-ylthio)carbapenems

  摘要：

  Structure-activity relationship studies of 1beta-methyl-2-[(3S,5R)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio]carbapenems, especially those pertaining to the relationship between antibacterial activity and side-chain structure were conducted. These studies suggested that the trans-(3S,5R)-5-phenylpyrrolidin-3-ylthio side-chain and the aminomethyl group at the 4-position of the phenyl ring play a key role in enhancing the antibacterial activity against the MRSA and Pseudomonas aeruginosa strains. In particular, the basicity of a substituent at the 4-position of the phenyl ring were shown to greatly contribute to the antibacterial activity against MRSA and methicillin-resistant Staphlyloccocus epidermidis strains. In contrast, the amidine group was shown to lead to potent antibacterial activity against P. aeruginosa strains comparable to that of imipenem, however, a good correlation between the basicity of the 4-substituent and antipseudomonal activity was not observed. In conclusion, the 4-aminomethyl or methylaminomethyl group on the phenyl ring was the best substituent for antipseudomonal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00430-8