(2R,3S,4S,5R)-1-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine-2-carbonitrile | 1147545-73-0

• 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: (2R,3S,4S,5R)-1-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine-2-carbonitrile
• CAS: 1147545-73-0
• 化学式: C₃₄H₃₄N₂O₃
• 分子量: 518.656
• InChiKey: NVZIRKFZCKHFKG-WZJLIZBTSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  649.5±55.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-1-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine-2-carbonitrile 在 盐酸 、 palladium 10% on activated carbon 、 METHYLTITANIUM TRIISOPROPOXIDE 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (2R,3S,4S,5R)-2-(1-aminocyclopropyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol dihydrochloride
  参考文献：
  名称：

  Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions

  摘要：

  The titanium-mediated cyclopropanation reaction using Ti((OPr)-Pr-i)(3)Me/EtMgBr/BF3 center dot OEt2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2S,3S,4R,5S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (38), which has the same absolute configuration as L-fucose, is a moderate (IC50=44 mu M), but selective, inhibitor of alpha-L-fucosidase from human placenta. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.024
• 作为产物：
  描述：

  1-N-benzylamino-1-C-cyano-2,3,5-tri-O-benzyl-L-arabinose 在 吡啶 、 甲基磺酰氯 作用下， 反应 1.0h， 以84%的产率得到(2R,3S,4S,5R)-1-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  5-取代的3，4-二羟基氰基吡咯烷的合成。容易获得聚羟基脯氨酸

  摘要：

  提出了一种合成氰基吡咯烷的新方法。从方便地官能化的d-核糖，d-甘露糖，d-（l）-阿拉伯糖开始，以四个步骤有效地合成了化合物，总体上具有良好的收率。还描述了向脯氨酸衍生物的转化以及这些衍生物在有机催化中的初步评估。

  DOI：

  10.1016/j.tet.2009.01.108

文献信息

• Synthesis of 2-aminocyclopropyl pyrrolidines from glycoaminonitriles
  作者：Delphine Declerck、Solen Josse、Albert Nguyen Van Nhien、Denis Postel

  DOI：10.1016/j.tetlet.2009.02.135

  日期：2009.5

  We have developed an expedient method for the synthesis of 2-aminocyclopropyl pyrrolidines from carbohydrate-derived α-aminonitriles involving up to five or six steps, the key step being the titanium-mediated aminocyclopropanation on the aminonitrile moiety, followed by cleavage of the protecting groups.

  我们已经开发了一种从碳水化合物衍生的α-氨基腈合成2个氨基环丙基吡咯烷的简便方法，涉及多达五或六个步骤，关键步骤是在氨基腈部分进行钛介导的氨基环丙烷化，然后裂解保护基。
• Synthesis of 5-substituted-3,4-dihydroxycyanopyrrolidines. An easy access to polyhydroxyprolines
  作者：Marina Moura、Sébastien Delacroix、Denis Postel、Albert Nguyen Van Nhien

  DOI：10.1016/j.tet.2009.01.108

  日期：2009.4

  A novel procedure for the synthesis of cyanopyrrolidines is presented. Starting from conveniently functionalized d-ribose, d-mannose, d-(l)-arabinose, the compounds were efficiently synthesised in four steps in overall good yields. Transformation into proline derivatives and preliminary evaluation of these derivatives in organocatalysis is also described.

  提出了一种合成氰基吡咯烷的新方法。从方便地官能化的d-核糖，d-甘露糖，d-（l）-阿拉伯糖开始，以四个步骤有效地合成了化合物，总体上具有良好的收率。还描述了向脯氨酸衍生物的转化以及这些衍生物在有机催化中的初步评估。
• Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions
  作者：Delphine Declerck、Albert Nguyen Van Nhien、Solen Josse、Jan Szymoniak、Philippe Bertus、Claudia Bello、Pierre Vogel、Denis Postel

  DOI：10.1016/j.tet.2011.12.024

  日期：2012.2

  The titanium-mediated cyclopropanation reaction using Ti((OPr)-Pr-i)(3)Me/EtMgBr/BF3 center dot OEt2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2S,3S,4R,5S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (38), which has the same absolute configuration as L-fucose, is a moderate (IC50=44 mu M), but selective, inhibitor of alpha-L-fucosidase from human placenta. (C) 2011 Elsevier Ltd. All rights reserved.