(2S,1′R,3′S)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine | 874339-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,1′R,3′S)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine
• 英文别名: (2S,1'R,3'S)-N-benzyloxycarbonyl-2-(3',4'-epoxi-1'-hydroxybut-1'-yl)pyrrolidine；benzyl (2S)-2-[(1R)-1-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]pyrrolidine-1-carboxylate
• CAS: 874339-89-6
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: WASDTZXEQCWZLX-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,1′R,3′S)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine
  参考文献：
  名称：

  A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes

  摘要：

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.010
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 indium 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.25h， 生成 (2S,1′R,3′S)-2-(3′,4′-epoxy-1′-hydroxbut-1′-yl)-1-(carbobenzyloxy)pyrrolidine
  参考文献：
  名称：

  A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes

  摘要：

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.010

文献信息

• Facile, Stereocontrolled Synthetic Route towards Bis-functionalised Pyrrolizidines
  作者：Janusz Jurczak、Marcin Lindner、Antoni Krasiński

  DOI：10.1055/s-0037-1609582

  日期：2018.11

  Ligands, and Targets Abstract A simple and convenient method for the synthesis of bis-functionalised pyrrolizidines starting from readily available N-Cbz-l-prolinal is described. This aldehyde was converted within two concise steps to the corresponding aminoepoxides, which were separately subjected to regioselective cyclisation induced by a reductive cleavage of the Cbz protecting group. The versatile

  作为特殊主题杂环的一部分作为催化剂，配体和靶标发布 抽象的 描述了一种从容易获得的N -Cbz- 1-脯氨酸开始合成双官能化吡咯烷核苷的简单方便的方法。在两个简洁的步骤中，将该醛转化为相应的氨基环氧化物，将其分别进行还原选择性裂解Cbz保护基团诱导的区域选择性环化。通用而简洁的策略在直接制备基于吡咯利嗪的药物和天然产品中具有巨大的实际应用潜力。 描述了一种从容易获得的N -Cbz- 1-脯氨酸开始合成双官能化吡咯烷核苷的简单方便的方法。在两个简洁的步骤中，将该醛转化为相应的氨基环氧化物，将其分别进行还原选择性裂解Cbz保护基团诱导的区域选择性环化。通用而简洁的策略在直接制备基于吡咯利嗪的药物和天然产品中具有巨大的实际应用潜力。
• A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes
  作者：Isidoro Izquierdo、María T. Plaza、Víctor Yáñez

  DOI：10.1016/j.tetasy.2005.10.010

  日期：2005.11

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.