(4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((R)-1-hydroxy-2-methyl-propyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 191920-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((R)-1-hydroxy-2-methyl-propyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 191920-63-5
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: QVSMIBCLSWXFNY-KHBBOIOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  87.07
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((R)-1-hydroxy-2-methyl-propyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 sodium 2-ethylhexanoic acid 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((R)-1-hydroxy-2-methyl-propyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of 2α-functionalized 1β-methylcarbapenems related to KR-21012

  摘要：

  The 2 alpha-functionalized 1 beta-merhylcarbapenems 3 were synthesized from the 2-formyl 1 beta-methylcarbapenem intermediate 5. The best compound in the series of 2 alpha-(hydroxy)alkylcarbapenems, KR-21012, displayed well balanced in vitro and in vivo activity as a parent compound of oral carbapenem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00692-7
• 作为产物：
  描述：

  prop-2-enyl (4S,5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-formyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 potassium fluoride 、 四丁基溴化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((R)-1-hydroxy-2-methyl-propyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of 2α-functionalized 1β-methylcarbapenems related to KR-21012

  摘要：

  The 2 alpha-functionalized 1 beta-merhylcarbapenems 3 were synthesized from the 2-formyl 1 beta-methylcarbapenem intermediate 5. The best compound in the series of 2 alpha-(hydroxy)alkylcarbapenems, KR-21012, displayed well balanced in vitro and in vivo activity as a parent compound of oral carbapenem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00692-7