(2R,4R)-2-(5-Hydroxymethyl-1-methyl-1H-pyrazol-3-ylmethyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid allyl ester | 164162-23-6

• 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: (2R,4R)-2-(5-Hydroxymethyl-1-methyl-1H-pyrazol-3-ylmethyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (2R,4R)-2-[[5-(hydroxymethyl)-1-methylpyrazol-3-yl]methyl]-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 164162-23-6
• 化学式: C₁₅H₂₃N₃O₆S
• 分子量: 373.43
• InChiKey: PQLZHWKSMLXKIZ-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-(5-Hydroxymethyl-1-methyl-1H-pyrazol-3-ylmethyl)-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid allyl ester 在 N,N-二甲基乙酰胺 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 3-{(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}-5-hydroxymethyl-1,2-dimethyl-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：

  (2R,4R)-2-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methyl-1H-pyrazol-3-ylmethyl]-4-hydroxy-pyrrolidine-1-carboxylic acid allyl ester 在 盐酸 作用下， 生成 (2R,4R)-2-(5-Hydroxymethyl-1-methyl-1H-pyrazol-3-ylmethyl)-4-methanesulfonyloxy-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.