(3R,4R)-[4-benzyloxy-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]methanol | 397883-75-9

• 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: (3R,4R)-[4-benzyloxy-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]methanol
• 英文别名: [(3R,4R)-1-[(1S)-1-phenylethyl]-4-phenylmethoxypyrrolidin-3-yl]methanol
• CAS: 397883-75-9
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: MGFOCZOLVSFGNW-DBVUQKKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-[4-benzyloxy-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]methanol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 336000.0h， 以99%的产率得到(3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition

  摘要：

  Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoyleamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compound can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxy- methyl)pyrrolidin-3-ol and its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00367-6
• 作为产物：
  描述：

  (S)-(-)-N-甲氧基甲基-N-(三甲基硅烷基)甲基-1-苯基乙胺 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3R,4R)-[4-benzyloxy-1-[(S)-1-phenylethyl]pyrrolidin-3-yl]methanol
  参考文献：
  名称：

  Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition

  摘要：

  Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoyleamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compound can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxy- methyl)pyrrolidin-3-ol and its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00367-6

文献信息

• Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1016/s0957-4166(01)00367-6

  日期：2001.8

  Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoyleamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compound can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxy- methyl)pyrrolidin-3-ol and its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.