(2S,3R)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3R)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid
• 英文别名: (2S,3R)-3-phenyl-2-(phenylmethoxycarbonylamino)pent-4-enoic acid
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: BPNLXDBARIUJCU-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-benzyloxycarbonylamino-3-phenyl-1-oxo-4-pentenyl)-pyrrolidine 在 Lithium-tri-methoxy-alanat 、 sodium chlorite 、 2-甲基-2-丁烯 、 溶剂黄146 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以59.8%的产率得到(2S,3R)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid
  参考文献：
  名称：

  Synthesis of Anti-β-Substituted γ,δ-Unsaturated Amino Acids via Eschenmoser−Claisen Rearrangement

  摘要：

  Anti-beta-substituted gamma,delta-unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.

  DOI：

  10.1021/ol061414l

文献信息

• Enantioselective Synthesis of <i>anti</i>-β-Substituted γ,δ-Unsaturated Amino Acids: A Highly Selective Asymmetric Thio-Claisen Rearrangement
  作者：Zhihua Liu、Hongchang Qu、Xuyuan Gu、Byoung J. Min、Joel Nyberg、Victor J. Hruby

  DOI：10.1021/ol801657q

  日期：2008.9.18

  novel synthesis of optically active anti-beta-substituted gamma,delta-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.

  通过硫代-克莱森重排实现了一种新型的光学活性抗 β 取代 γ、δ 不饱和氨基酸的合成。使用 2,5-二苯基吡咯烷作为 C2 对称手性助剂来控制立体化学，获得良好的产率和优异的非对映选择性和对映选择性。
• Asymmetric Eschenmoser−Claisen Rearrangement for Anti-β-Substituted γ,δ-Unsaturated Amino Acids
  作者：Hongchang Qu、Xuyuan Gu、Zhihua Liu、Byoung J. Min、Victor J. Hruby

  DOI：10.1021/ol701704h

  日期：2007.9.1

  synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.

  光学活性的抗β-取代的γ，δ-不饱和氨基酸是有机合成和拟肽过程中重要的合成基石。一种新型的不对称Eschenmoser-Claisen重排使用C2对称手性助剂被开发来生成这种类型的氨基酸。通过碘代内酯化/锌还原除去手性助剂后，获得了极好的非对映选择性和高对映选择性（87-93％ee）。
• Synthesis of Anti-β-Substituted γ,δ-Unsaturated Amino Acids via Eschenmoser−Claisen Rearrangement
  作者：Hongchang Qu、Xuyuan Gu、Byoung J. Min、Zhihua Liu、Victor J. Hruby

  DOI：10.1021/ol061414l

  日期：2006.9

  Anti-beta-substituted gamma,delta-unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.