(6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane | 117811-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane
• 英文别名: (7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-6,7,8,8a-tetrahydro-1H-pyrrolo[2,1-c][1,4]oxazin-4-one
• CAS: 117811-71-9
• 化学式: C₁₃H₂₅NO₃Si
• 分子量: 271.432
• InChiKey: SJHXMMGCINMZHK-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane 在 盐酸 、 sodium hydroxide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (2S,4R)-4-methanesulfonyloxy-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
  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：

  (2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 在 palladium dihydroxide 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 38.0h， 生成 (6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane
  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

• 3-pyrrolidinylthio-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04822787A1

  公开（公告）日：1989-04-18

  This invention consists of 3-pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and their use as antimicrobial agents in the treatment of infectious diseases.

  这项发明包括3-吡咯烷基巯基-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸化合物及其用作治疗传染病的抗菌剂的应用。
• 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US04983596A1

  公开（公告）日：1991-01-08

  The invention relates to a compound of antimicrobial activity, of the formula: ##STR1## in which R.sup.1 is carboxy or protected carboxy, R.sup.2 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is 2-fluoroethyl, 2-chloroethyl, 2-fluoropropyl or 4-fluorobutyl, R.sup.5 is hydrogen, lower alkanimidoyl, unsubstituted lower cycloalkenyl or substituted by a group consisting of oxo and amino, or imino-protective group, and A is lower alkylene, or pharmaceutically acceptable salts thereof.

  该发明涉及一种具有抗微生物活性的化合物，其化学式为：##STR1##其中R.sup.1是羧基或保护羧基，R.sup.2是羟基(较低)烷基或保护羟基(较低)烷基，R.sup.3是氢或较低烷基，R.sup.4是2-氟乙基，2-氯乙基，2-氟丙基或4-氟丁基，R.sup.5是氢，较低烷基亚胺基，未取代的较低环烯基或由氧代和氨基组成的取代基，或亚胺保护基，A是较低烷基，或其药用可接受盐。