(2S,4R)-1-Allyloxycarbonyl-2-(4-fluorobutyl)oxymethyl-4-methanesulfonyloxypyrrolidine | 127791-58-6

• 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: (2S,4R)-1-Allyloxycarbonyl-2-(4-fluorobutyl)oxymethyl-4-methanesulfonyloxypyrrolidine
• 英文别名: prop-2-enyl (2S,4R)-2-(4-fluorobutoxymethyl)-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 127791-58-6
• 化学式: C₁₄H₂₄FNO₆S
• 分子量: 353.412
• InChiKey: OCMHRCURBUJWPR-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-Allyloxycarbonyl-2-(4-fluorobutyl)oxymethyl-4-methanesulfonyloxypyrrolidine 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 8.75h， 生成 allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(4-fluorobutyl)oxymethylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems—I. 2-alkoxymethyl derivatives

  摘要：

  The synthesis and in vitro antibacterial activity of a novel series of 2-alkoxymethyl-4-pyrrolidinylthio-1 beta-methyl carbapenems are described. As a result of these studies, we discovered that FR27743 (19j) containing a novel,2-fluoroethoxymethyl substituent possesses a broad spectrum of antibacterial activity against both Gram-positive and Gram-negative organisms, including Pseudomonas aeruginosa. Furthermore, FR27743 exhibited excellent stability against renal dehydropeptidase-I (DHP-I), good urinary recovery, and superior in vivo activity compared to that for Meropenem against several systemic infections. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00142-9
• 作为产物：
  描述：

  Cbz-L-羟脯氨酸 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 草酰氯 、 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 、 硫酸 、 三氟化硼乙醚 、 potassium tert-butylate 、 氢气 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 38.25h， 生成 (2S,4R)-1-Allyloxycarbonyl-2-(4-fluorobutyl)oxymethyl-4-methanesulfonyloxypyrrolidine
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems—I. 2-alkoxymethyl derivatives

  摘要：

  The synthesis and in vitro antibacterial activity of a novel series of 2-alkoxymethyl-4-pyrrolidinylthio-1 beta-methyl carbapenems are described. As a result of these studies, we discovered that FR27743 (19j) containing a novel,2-fluoroethoxymethyl substituent possesses a broad spectrum of antibacterial activity against both Gram-positive and Gram-negative organisms, including Pseudomonas aeruginosa. Furthermore, FR27743 exhibited excellent stability against renal dehydropeptidase-I (DHP-I), good urinary recovery, and superior in vivo activity compared to that for Meropenem against several systemic infections. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00142-9

文献信息

• US4983596A
  申请人：——

  公开号：US4983596A

  公开（公告）日：1991-01-08
• Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems—I. 2-alkoxymethyl derivatives
  作者：Hidenori Azami、Hideo Tsutsumi、Keiji Matsuda、David Barrett、Kouji Hattori、Takashi Nakajima、Satoru Kuroda、Toshiaki Kamimura、Masayoshi Murata

  DOI：10.1016/s0968-0896(97)00142-9

  日期：1997.11

  The synthesis and in vitro antibacterial activity of a novel series of 2-alkoxymethyl-4-pyrrolidinylthio-1 beta-methyl carbapenems are described. As a result of these studies, we discovered that FR27743 (19j) containing a novel,2-fluoroethoxymethyl substituent possesses a broad spectrum of antibacterial activity against both Gram-positive and Gram-negative organisms, including Pseudomonas aeruginosa. Furthermore, FR27743 exhibited excellent stability against renal dehydropeptidase-I (DHP-I), good urinary recovery, and superior in vivo activity compared to that for Meropenem against several systemic infections. (C) 1997 Elsevier Science Ltd.