(2R,4R)-1-tert-butoxycarbonyl-2-[4-[(S)-1-tert-butoxycarbonylamino-2-tert-butoxycarbonylethyl]phenyl]-4-hydroxypyrrolidine | 312297-51-1

• 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-2-[4-[(S)-1-tert-butoxycarbonylamino-2-tert-butoxycarbonylethyl]phenyl]-4-hydroxypyrrolidine
• 英文别名: tert-butyl (2R,4R)-4-hydroxy-2-[4-[(1S)-3-[(2-methylpropan-2-yl)oxy]-1-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenyl]pyrrolidine-1-carboxylate
• CAS: 312297-51-1
• 化学式: C₂₇H₄₂N₂O₇
• 分子量: 506.64
• InChiKey: HAJGATCEZBTPPP-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-tert-butoxycarbonyl-2-[4-[(S)-1-tert-butoxycarbonylamino-2-tert-butoxycarbonylethyl]phenyl]-4-hydroxypyrrolidine 在 ammonium hydroxide 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.33h， 生成 (2R,4S)-4-acetylthio-1-tert-butoxycarbonyl-2-[4-[(S)-1-tert-butoxycarbonylamino-2-carbamoylethyl]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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (2R,4R)-2-[4-[1-amino-2-tert-butoxycarbonylethyl]phenyl]-1-tert-butoxycarbonyl-4-hydroxypyrrolidine acetic acid 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到(2R,4R)-1-tert-butoxycarbonyl-2-[4-[(S)-1-tert-butoxycarbonylamino-2-tert-butoxycarbonylethyl]phenyl]-4-hydroxypyrrolidine
  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.