allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate | 312297-55-5

• 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: allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
• 英文别名: prop-2-enyl (4R,5S,6S)-3-[(3S,5R)-5-[4-[(1S)-3-amino-3-oxo-1-(prop-2-enoxycarbonylamino)propyl]phenyl]-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 312297-55-5
• 化学式: C₃₄H₄₂N₄O₉S
• 分子量: 682.795
• InChiKey: SOUVHQNFQNWPSO-UMETUBOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  203
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate 在 (PPh₃)2PCl₂ 、 水 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以74.5%的产率得到J-114,870
  参考文献：
  名称：

  Stereoselective Synthesis of a Broad Spectrum 1β-Methylcarbapenem, J-114,870

  摘要：

  An ultra-broad spectrum carbapenem, J-114,870 (1), was synthesized from the corresponding C-2 side chain and 1 beta-methyl carbapenem enolphosphate. Synthesis of the C-2 side chain was accomplished by installation of the benzene part to (4R)-hydroxy-2-pyrrolidone 3, affording 2-phenylpyrrolidine 8a, and asymmetric Michael addition of chiral amine to alpha,beta-unsaturated ester derived from 8a. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00685-2
• 作为产物：
  描述：

  (2R,4S)-4-acetylthio-1-tert-butoxycarbonyl-2-[4-[(S)-1-tert-butoxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidine 在 盐酸 、 sodium hydroxide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 6.5h， 生成 allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-[(S)-1-allyloxycarbonylamino-2-carbamoylethyl]phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of a Broad Spectrum 1β-Methylcarbapenem, J-114,870

  摘要：

  An ultra-broad spectrum carbapenem, J-114,870 (1), was synthesized from the corresponding C-2 side chain and 1 beta-methyl carbapenem enolphosphate. Synthesis of the C-2 side chain was accomplished by installation of the benzene part to (4R)-hydroxy-2-pyrrolidone 3, affording 2-phenylpyrrolidine 8a, and asymmetric Michael addition of chiral amine to alpha,beta-unsaturated ester derived from 8a. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00685-2