(4S,5S)-4-carboxymethyl-2-oxo-1-azabicyclo[3,3,0]octane | 204912-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (4S,5S)-4-carboxymethyl-2-oxo-1-azabicyclo[3,3,0]octane
• 英文别名: 2-[(1S,8S)-3-oxo-1,2,5,6,7,8-hexahydropyrrolizin-1-yl]acetic acid
• CAS: 204912-57-2
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: FUQLMROUCGKAPD-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 (4S,5S)-4-carboxymethyl-2-oxo-1-azabicyclo[3,3,0]octane 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到(1S,8S)-(-)-ethyl hexahydro-3-oxo-3H-pyrrolizin-1-ylacetate
  参考文献：
  名称：

  An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step

  摘要：

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00007-6
• 作为产物：
  描述：

  3-((S)-1-Benzyloxycarbonyl-pyrrolidin-2-yl)-pentanedioic acid diethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (4S,5S)-4-carboxymethyl-2-oxo-1-azabicyclo[3,3,0]octane
  参考文献：
  名称：

  An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step

  摘要：

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00007-6

文献信息

• An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step
  作者：Norikazu Ohtake、Yasuyuki Imai、Ryosuke Ushijima

  DOI：10.1016/s0040-4020(98)00007-6

  日期：1998.3

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.