(2R,4S)-2-(1-Methyl-1H-pyrazol-4-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester | 164161-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,4S)-2-(1-Methyl-1H-pyrazol-4-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (2R,4S)-2-[(1-methylpyrazol-4-yl)methyl]-4-tritylsulfanylpyrrolidine-1-carboxylate
• CAS: 164161-77-7
• 化学式: C₃₂H₃₃N₃O₂S
• 分子量: 523.699
• InChiKey: LZZGWTCCKBHAEJ-IHLOFXLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-(1-Methyl-1H-pyrazol-4-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester 在 甲醇 、 三乙基硅烷 、 N,N-二甲基乙酰胺 、 Amberlist A-26 、 氨 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 4-{(2R,4S)-1-Allyloxycarbonyl-4-[(4R,5S,6S)-2-allyloxycarbonyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-1-carboxymethyl-2-methyl-2H-pyrazol-1-ium; chloride
  参考文献：
  名称：

  Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00230-8
• 作为产物：
  描述：

  (RS)-[(2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-4-yl)methanol 在 三正丁基氢锡 、 sodium methylate 、 硫代氯甲酸苯酯 作用下， 生成 (2R,4S)-2-(1-Methyl-1H-pyrazol-4-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00230-8

文献信息

• Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs
  作者：Hidenori Azami、David Barrett、Akira Tanaka、Hiroshi Sasaki、Keiji Matsuda、Minoru Sakurai、Yoshimi Matsumoto、Shuichi Tawara、Toshiyuki Chiba、Kazuo Sakane

  DOI：10.1016/s0960-894x(97)00230-8

  日期：1997.6

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.