(2R,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-[4-[(S)-1-[(R)-N-benzyl-N-(α-methylbenzyl)amino]-2-tert-butoxycarbonylethyl]phenyl]pyrrolidine | 312297-46-4

• 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: (2R,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-[4-[(S)-1-[(R)-N-benzyl-N-(α-methylbenzyl)amino]-2-tert-butoxycarbonylethyl]phenyl]pyrrolidine
• 英文别名: tert-butyl (2R,4R)-2-[4-[(1S)-1-[benzyl-[(1R)-1-phenylethyl]amino]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]phenyl]-4-hydroxypyrrolidine-1-carboxylate
• CAS: 312297-46-4
• 化学式: C₃₇H₄₈N₂O₅
• 分子量: 600.799
• InChiKey: RNYHSMUKEHRJJK-SQOZHWTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 (2R,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-[4-[(S)-1-[(R)-N-benzyl-N-(α-methylbenzyl)amino]-2-tert-butoxycarbonylethyl]phenyl]pyrrolidine 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、354.64 kPa 条件下， 反应 20.0h， 生成 (2R,4R)-2-[4-[(R)-1-amino-2-tert-butoxycarbonylethyl]phenyl]-1-tert-butoxycarbonyl-4-hydroxypyrrolidine acetic acid 、 (2R,4R)-2-[4-[(S)-1-amino-2-tert-butoxycarbonylethyl]phenyl]-1-tert-butoxycarbonyl-4-hydroxypyrrolidine acetic acid
  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,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-formylphenyl)pyrrolidine 在 正丁基锂 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (2R,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-[4-[(S)-1-[(R)-N-benzyl-N-(α-methylbenzyl)amino]-2-tert-butoxycarbonylethyl]phenyl]pyrrolidine
  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

文献信息

• Stereoselective Synthesis of a Broad Spectrum 1β-Methylcarbapenem, J-114,870
  作者：Hideaki Imamura、Aya Shimizu、Hiroki Sato、Yuichi Sugimoto、Shunji Sakuraba、Shigeru Nakajima、Shinnosuke Abe、Keiko Miura、Ikuko Nishimura、Koji Yamada、Hajime Morishima

  DOI：10.1016/s0040-4020(00)00685-2

  日期：2000.9

  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.