(2R,4R)-1-tert-butoxycarbonyl-2-[4-[(E)-2-(tert-butoxycarbonyl)vinyl]phenyl]-4-hydroxypyrrolidine | 312297-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2R,4R)-1-tert-butoxycarbonyl-2-[4-[(E)-2-(tert-butoxycarbonyl)vinyl]phenyl]-4-hydroxypyrrolidine
• 英文别名: tert-butyl (2R,4R)-4-hydroxy-2-[4-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]pyrrolidine-1-carboxylate
• CAS: 312297-45-3
• 化学式: C₂₂H₃₁NO₅
• 分子量: 389.492
• InChiKey: UDMNAVAVMBGLHW-PQGVJJGYSA-N

物化性质

• 沸点：
  516.6±50.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-tert-butoxycarbonyl-2-[4-[(E)-2-(tert-butoxycarbonyl)vinyl]phenyl]-4-hydroxypyrrolidine 在 palladium dihydroxide 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -77.0~20.0 ℃ 、354.64 kPa 条件下， 反应 21.0h， 生成 (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 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,4R)-1-tert-butoxycarbonyl-2-[4-[(E)-2-(tert-butoxycarbonyl)vinyl]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

• Synthesis of the Side Chain of a Novel Carbapenem via Iodine-Mediated Oxidative Cyclization of (1R)-N-(1-Aryl-3-butenyl)acetamide.
  作者：Takashi Hashihayata、Hiroki Sakoh、Yasuhiro Goto、Koji Yamada、Hajime Morishima

  DOI：10.1248/cpb.50.423

  日期：——

  A (2R,4S)-trans-disubstituted pyrrolidine ring system was constructed by employing iodine-mediated oxidative cyclization of (1R)-N-[1-(4-bromophenyl)-3-butenyl]acetamide 3 as a key step. The resulting diastereomeric mixture of (2R)-2-aryl-4-acetoxypyrrolidine 4 was stereoselectively converted to the side-chain of a novel ultra-broad-spectrum carbapenem 1, via (2R,4R)-2-aryl-4-hydroxypyrrolidine 7.

  以(1R)-N-[1-(4-溴苯基)-3-丁烯基]乙酰胺3的碘介导氧化环化为关键步骤，构建了(2R,4S)-反式-二取代吡咯烷环体系。所得的(2R)-2-芳基-4-乙酰氧基吡咯烷4的非对映异构体混合物通过(2R,4R)-2-芳基-4-羟基吡咯烷立体选择性地转化为新型超广谱碳青霉烯1的侧链7.