Boc-Val-ΔAla-OMe | 158068-95-2

• 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: Boc-Val-ΔAla-OMe
• 英文别名: methyl 2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]prop-2-enoate
• CAS: 158068-95-2
• 化学式: C₁₄H₂₄N₂O₅
• 分子量: 300.355
• InChiKey: UJTVIUBLUNCQIM-JTQLQIEISA-N

物化性质

• 沸点：
  468.0±45.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯基三甲氧基硅烷 、 Boc-Val-ΔAla-OMe 在 [Rh(COD)2][BF₄] 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以68%的产率得到Boc-Val-DL-Phe-OMe
  参考文献：
  名称：

  Peptide modification through site-selective residue interconversion: application of the rhodium-catalysed 1,4-addition of aryl siloxanes and boronates

  摘要：

  The site-selective interconversion of serine and cysteine residues of di- and tripeptides into phenylalanine derivatives, bearing a range of functionalities, has been achieved in high yield and selectivity through the common dehydroalanine intermediate. Through the application and development of the rhodium-catalysed 1,4-addition to alpha,beta-dehydroamino acid moieties with organometallic nucleophiles, a variety of peptides have been successfully modified to contain unnatural amino acid residues in predesignated residue positions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.067
• 作为产物：
  描述：

  methyl (tert-butoxycarbonyl)-L-valyl-L-serinate 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到Boc-Val-ΔAla-OMe
  参考文献：
  名称：

  Peptide modification through site-selective residue interconversion: application of the rhodium-catalysed 1,4-addition of aryl siloxanes and boronates

  摘要：

  The site-selective interconversion of serine and cysteine residues of di- and tripeptides into phenylalanine derivatives, bearing a range of functionalities, has been achieved in high yield and selectivity through the common dehydroalanine intermediate. Through the application and development of the rhodium-catalysed 1,4-addition to alpha,beta-dehydroamino acid moieties with organometallic nucleophiles, a variety of peptides have been successfully modified to contain unnatural amino acid residues in predesignated residue positions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.067

文献信息

• Cyclopropanation using flow-generated diazo compounds
  作者：Nuria M. Roda、Duc N. Tran、Claudio Battilocchio、Ricardo Labes、Richard J. Ingham、Joel M. Hawkins、Steven V. Ley

  DOI：10.1039/c5ob00019j

  日期：——

  A practical and mild protocol for the cyclopropanation of unstabilised diazo compounds is reported.

  一种实用且温和的方法用于环丙烷化不稳定的重氮化合物。
• Versatile Ru‐Photoredox‐Catalyzed Functionalization of Dehydro‐Amino Acids and Peptides
  作者：Tobias Brandhofer、Olga García Mancheño

  DOI：10.1002/cctc.201900446

  日期：2019.8.21

  A versatile photoredox‐catalyzed synthesis of unnatural amino acids and peptides is presented. Commercially available Ru(bpy)3(PF6)2 was efficiently used as visible light photocatalyst in combination with a broad number of different types of radical precursors in the coupling with several dehydrogenated amino acid residues. This method provides new entries to the mild, selective and direct modification

  提出了一种通用的光氧化还原催化的非天然氨基酸和肽的合成方法。在与几个脱氢氨基酸残基偶合的过程中，将市售的Ru（bpy）3（PF 6）2与多种不同类型的自由基前体组合有效地用作可见光光催化剂。该方法为简单和复杂的肽样化合物向具有改进或异常特性的新型结构的温和，选择性和直接修饰提供了新的思路。因此，（氟化）烷基卤化物，芳基磺酰氯或各种N-（酰氧基）邻苯二甲酰亚胺（NHPI酯）与一系列天然和非天然的α，β-脱氢氨基酸和二肽有效反应。而且，该方法的适用性还通过天然存在的肽硫代链丝菌肽的后期功能化来证明。
• Direct Photoexcitable Iodomethylborate Enabling Cyclopropanation of Reactive Alkenes
  作者：Rikako Nakamura、Yuto Sumida、Hirohisa Ohmiya

  DOI：10.1246/bcsj.20220112

  日期：2022.7.15

  Radical-mediated cyclopropanation tool for reactive alkenes including dehydroamino acids (DHAAs) has been developed based on directly photoexcitable borate generating iodomethyl radical under visible light irradiation. The borate at the excited state serves as a strong single electron reductant. Therefore, this photoexcitable borate offers a simple protocol for cyclopropanation of DHAAs to forge m

  基于在可见光照射下直接光激发硼酸盐产生碘甲基自由基，开发了自由基介导的用于反应性烯烃（包括脱氢氨基酸（DHAA））的环丙烷化工具。处于激发态的硼酸盐用作强单电子还原剂。因此，这种可光激发的硼酸盐为 DHAA 的环丙烷化提供了一种简单的方案，以形成具有药用价值的环丙烷氨基酸。
• Total synthesis of (−)-bistatramide C
  作者：Enrique Aguilar、A.I. Meyers

  DOI：10.1016/s0040-4039(00)77148-6

  日期：1994.4

  The total synthesis of macrocyclic hexapeptide Bistatramide C is reported from enantiomerically pure oxazole and thiazole amino acids.
• Visible-Light Mediated Deoxygenation of Carboxylic Acid for Late-Stage Peptide Modification Targeting Dehydroalanine
  作者：Guangjun Bao、Peng Wang、Xiaomin Guo、Yiping Li、Zeyuan He、Xinyi Song、Ruiyao E、Tingli Yu、Junqiu Xie、Wangsheng Sun

  DOI：10.1021/acs.orglett.3c03453

  日期：2023.11.24