(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester | 366498-33-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S,3S,5S)-3-phenyl-5-[(E)-prop-1-enyl]pyrrolidine-1,2-dicarboxylate
• CAS: 366498-33-1
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: POZBKSMHWBANDG-OAHMWZIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester 在 lithium diisopropyl amide 、 甲醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 以80%的产率得到(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-D-proline methyl ester
  参考文献：
  名称：

  Building constrained peptidomimetics: a convenient approach to 3-phenyl-5-vinyl substituted proline derivatives

  摘要：

  An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00532-4
• 作为产物：
  描述：

  (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester 在 4-甲基苯磺酸吡啶 、 lithium 作用下， 以 乙醚 为溶剂， 反应 27.25h， 生成 (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester
  参考文献：
  名称：

  Building constrained peptidomimetics: a convenient approach to 3-phenyl-5-vinyl substituted proline derivatives

  摘要：

  An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00532-4

文献信息

• Building constrained peptidomimetics: a convenient approach to 3-phenyl-5-vinyl substituted proline derivatives
  作者：Shengquan Duan、Kevin D Moeller

  DOI：10.1016/s0040-4020(01)00532-4

  日期：2001.7

  An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines. (C) 2001 Elsevier Science Ltd. All rights reserved.