(S)-N^α-tert-butyloxycarbonyl-m-phenyltyrosine | 906356-20-5

• 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: (S)-N^α-tert-butyloxycarbonyl-m-phenyltyrosine
• 英文别名: N-boc-3-phenyltyrosine；(2S)-3-(4-hydroxy-3-phenylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 906356-20-5
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: OGGNGUVTIBMFEP-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N^α-tert-butyloxycarbonyl-m-phenyltyrosine 、 Fmoc-D-缬氨酸 生成 (2R)-2-[[(2S)-2-amino-3-(4-hydroxy-3-phenylphenyl)propanoyl]amino]-3-methylbutanoic acid
  参考文献：
  名称：

  Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives

  摘要：

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.

  DOI：

  10.1021/jo060704c
• 作为产物：
  描述：

  Boc-l-3-碘酪氨酸 在 palladium diacetate 、 palladium on activated charcoal 氢气 、 sodium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 乙二醇二甲醚 、 N,N-二甲基乙酰胺 、 水 、 丙酮 为溶剂， 20.0~80.0 ℃ 、100.0 kPa 条件下， 反应 11.0h， 生成 (S)-N^α-tert-butyloxycarbonyl-m-phenyltyrosine
  参考文献：
  名称：

  Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives

  摘要：

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.

  DOI：

  10.1021/jo060704c

文献信息

• A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water
  作者：Arnaud Peramo、Ibrahim Abdellah、Shannon Pecnard、Julie Mougin、Cyril Martini、Patrick Couvreur、Vincent Huc、Didier Desmaële

  DOI：10.3390/molecules25061459

  日期：——

  (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4′-arylated

  发现用N-杂环卡宾（NHC）-钯配合物功能化的纳米杯[8]芳烃是水溶性碘代和溴代芳基化合物与环状三醇芳基硼酸酯在低温下进行Suzuki-Miyaura交叉偶联反应的有效纳米反应器。水，不含任何有机助溶剂。结合改进的从硼酸一步合成三醇芳基硼酸酯的方法，这一非常高效的新工具以低催化剂负载量和广泛的官能团耐受性，以良好的产率提供了多种 4'-芳基化苯丙氨酸和酪氨酸。
• PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water
  作者：Anaëlle Dumas、Arnaud Peramo、Didier Desmaële、Patrick Couvreur

  DOI：10.2533/chimia.2016.252

  日期：——

  desirable tools to track biomolecules and manipulate complex biological processes. Here, we report a new nanocatalyst consisting of small palladium nanoparticles stabilized on the surface of PLGA-PEG nanoparticles that show excellent catalytic activity for the modification of biological building blocks through Suzuki-Miyaura cross-coupling reactions in water. Brominated or iodinated amino acids were coupled

  可以在生理条件下选择性进行的化学转化是追踪生物分子和操纵复杂生物过程的非常理想的工具。在这里，我们报告了一种新型的纳米催化剂，该催化剂由稳定在PLGA-PEG纳米颗粒表面上的小钯纳米颗粒组成，这些纳米颗粒在水中通过Suzuki-Miyaura交叉偶联反应显示出出色的催化活性，可用于修饰生物构件。将溴化或碘化​​氨基酸与芳基硼酸在磷酸盐缓冲液中偶联，收率很高。有趣的是，仅在1摩尔％的钯存在下，使用稳定的水溶性环状三硼硼酸盐作为有机金属伴侣，在37°C的2小时内可实现高达98％的转化为偶联氨基酸。
• Selective modification of a native protein in a patient tissue homogenate using palladium nanoparticles
  作者：Arnaud Peramo、Anaëlle Dumas、Hynd Remita、Mireille Benoît、Stephanie Yen-Nicolay、Raphaël Corre、Ruy A. Louzada、Corinne Dupuy、Shannon Pecnard、Benoit Lambert、Jacques Young、Didier Desmaële、Patrick Couvreur

  DOI：10.1039/c9cc07803g

  日期：——

  A chemoselective native protein modification in near-organ medium was achieved using new benign palladium nanoparticles.

  在接近生物体介质中，利用新型良性钯纳米颗粒实现了对天然蛋白质的化学选择性修饰。
• A Convenient Catalyst for Aqueous and Protein Suzuki−Miyaura Cross-Coupling
  作者：Justin M. Chalker、Charlotte S. C. Wood、Benjamin G. Davis

  DOI：10.1021/ja907150m

  日期：2009.11.18

  A phosphine-free palladium catalyst for aqueous Suzuki-Miyaura cross-coupling is presented. The catalyst is active enough to mediate hindered, ortho-substituted biaryl couplings but mild enough for use on peptides and proteins. The 1 Suzuki-Miyaura couplings on protein substrates are the first to proceed in useful conversions. Notably, hydrophobic aryl and vinyl groups can be transferred to the protein surface without the aid of organic solvent since the aryl- and vinylboronic acids used in the coupling are water-soluble as borate salts. The convenience and activity of this catalyst prompts use in both general synthesis and bioconjugation.
• Efficient Enantioselective Synthesis of Condensed and Aromatic-Ring-Substituted Tyrosine Derivatives
  作者：Sebastian Knör、Burkhardt Laufer、Horst Kessler

  DOI：10.1021/jo060704c

  日期：2006.7.1

  An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected L-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. D-and L- 4- hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha- enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.