methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate | 366498-31-9

• 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: methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate
• 英文别名: methyl (2S,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpent-4-enoate
• CAS: 366498-31-9
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: CEIIDTUPXCMSHW-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate 在 三氟化硼四氢呋喃络合物 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-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
• 作为产物：
  描述：

  、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以2.7 g的产率得到methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate
  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

• Thiol-Ene Click Reactions - Versatile Tools for the Modification of Unsaturated Amino Acids and Peptides
  作者：Lisa Karmann、Uli Kazmaier

  DOI：10.1002/ejoc.201300672

  日期：2013.11

  Terminal γ,δ-unsaturated amino acids, easily available by Claisen rearrangement or palladium-catalysed allylic alkylation, are excellent substrates for radical thiol additions. These click reactions allow the introduction of highly functionalized side-chains into a given amino acid or peptide. This protocol is suitable for the modification of all kinds of terminal alkenes, such as allyl protecting

  末端 γ,δ-不饱和氨基酸很容易通过克莱森重排或钯催化的烯丙基烷基化获得，是自由基硫醇加成的极好底物。这些点击反应允许将高度功能化的侧链引入给定的氨基酸或肽中。该方案适用于各种末端烯烃的修饰，如烯丙基保护基团。
• Synthesis of Novel Quaternary Amino Acids Using Molybdenum-Catalyzed Asymmetric Allylic Alkylation
  作者：Barry M. Trost、Kalindi Dogra

  DOI：10.1021/ja020290e

  日期：2002.6.1

  also observed. In all cases, excellent diastereo- and enantioselectivity of the branched alkylated product are observed. This new asymmetric reaction provides ready access to unusual quarternary amino acids, important building blocks for biological applications. The reactions complements the Pd AAA wherein the cinnamyl substrate leads to only the product of attack at the primary terminus of the allyl

  使用吖内酯的 Mo 催化的不对称烯丙基烷基化提供了非凡的选择性。因此，范围广泛的肉桂基型底物与 2-甲基和 2-苄基吖内酯反应，仅产生由更多取代的碳攻击产生的产物。使用其他烷基取代基（例如 2-甲硫基乙基、异丁基、烯丙基和异丙基）提供的产物仍保留出色的区域选择性，但也观察到少量线性产物。在所有情况下，都观察到支链烷基化产物具有优异的非对映选择性和对映选择性。这种新的不对称反应可以方便地获取不寻常的四元氨基酸，这是生物学应用的重要组成部分。