methyl (R)-N-Boc-3-bromo-4-methoxyphenylglycinate | 192328-47-5

• 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: methyl (R)-N-Boc-3-bromo-4-methoxyphenylglycinate
• 英文别名: methyl (R)-N-(tert-butoxycarbonyl)-2-(3-bromo-4-methoxyphenyl)glycinate；Boc-(R)-3-bromo-4-hydroxyphenylglycine(OMe)-OMe；methyl (2R)-2-(3-bromo-4-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 192328-47-5
• 化学式: C₁₅H₂₀BrNO₅
• 分子量: 374.232
• InChiKey: VMFQBEKDVQPHSW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-N-Boc-3-bromo-4-methoxyphenylglycinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.3h， 以90%的产率得到methyl (2R)-2-amino-2-(3-bromo-4-methoxyphenyl)acetate
  参考文献：
  名称：

  Synthesis of the Vancomycin CD and DE Ring Systems

  摘要：

  Full details of the synthesis of the fully substituted vancomycin CD and DE ring systems are described and a potential solution to the control of the atropisomer stereochemistry is defined.

  DOI：

  10.1021/jo970560p
• 作为产物：
  描述：

  methyl (2R)-2-amino-2-(3-bromo-4-hydroxyphenyl)acetate 在 碳酸氢钠 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (R)-N-Boc-3-bromo-4-methoxyphenylglycinate
  参考文献：
  名称：

  Synthesis of Orthogonally Protected Actinoidic Acid Trimethyl Ether

  摘要：

  DOI：

  10.3987/com-18-s(f)2

文献信息

• Use of the SPhos Ligand to Suppress Racemization in Arylpinacolboronate Ester Suzuki Couplings Involving α-Amino Acids. Synthesis of Biaryl Derivatives of 4-Hydroxyphenylglycine, Tyrosine, and Tryptophan
  作者：Mònica Prieto、Silvia Mayor、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo901899w

  日期：2009.12.4

  α-Amino acid derivatives, particularly those of phenylglycine, can suffer significant racemization in Suzuki couplings. When arylpinacolboronate esters are used as coupling partners this unwanted side reaction can be suppressed by the use of Pd(OAc)2 as Pd(0) source, in the presence of Buchwald’s SPhos ligand. The syntheses of biaryl amino acids of tyrosine, phenylglycine, and tryptophan, including

  α-氨基酸衍生物，特别是苯基甘氨酸的衍生物，在Suzuki偶联中会遭受显着的消旋作用。当芳基频哪醇硼酸酯用作偶联伙伴时，在存在布赫瓦尔德氏SPhos配体的情况下，可以通过使用Pd（OAc）2作为Pd（0）来抑制这种有害的副反应。据报道，酪氨酸，苯基甘氨酸和色氨酸的联芳基氨基酸的合成，包括与天然肽中的氯肽家族相似的Phg-Trp单元。
• Next-Generation Total Synthesis of Vancomycin
  作者：Maxwell J. Moore、Shiwei Qu、Ceheng Tan、Yu Cai、Yuzo Mogi、D. Jamin Keith、Dale L. Boger

  DOI：10.1021/jacs.0c07433

  日期：2020.9.16

  A next-generation total synthesis of vancomycin aglycon is detailed that was achieved in 17 steps (longest linear sequence, LLS) from the constituent amino acid subunits with kinetically controlled diastereoselective introduction of all three elements of atropisomerism. In addition to new syntheses of three of the seven amino acid subunits, highlights of the approach include a ligand-controlled atroposelective

  详细介绍了万古霉素苷元的下一代全合成，该合成通过 17 个步骤（最长线性序列，LLS）从组成氨基酸亚基实现，并通过动力学控制非对映选择性引入所有三种阻转异构元素。除了七个氨基酸亚基中三个的新合成外，该方法的亮点包括配体控制的 atroposelective one-pot Miyaura 硼酸化-Suzuki 偶联序列，用于引入 AB 联芳基手性轴 (>20:1 dr)，几乎没有竞争性差向异构化 (>30:1 dr) 的 AB 环系统的基本瞬时和可扩展的大环内酰胺化，以及用于连续 CD (8:1 dr) 和 DE 环闭合的两个室温 atroposelective 分子内 SNAr 环化 (14: 1 dr）受益于预先形成的 AB 环系统的预组织和微妙的取代基效应。结合万古霉素苷元的无保护基两步酶促糖基化，这提供了万古霉素的 19 步全合成。该方法为大规模合成制备口袋修饰万古霉素类似物铺平了
• Racemization in Suzuki Couplings: A Quantitative Study Using 4-Hydroxyphenylglycine and Tyrosine Derivatives as Probe Molecules
  作者：Mònica Prieto、Silvia Mayor、Katy Rodríguez、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo0621266

  日期：2007.2.1

  Reaction conditions considered to be typical in Suzuki couplings can cause significant (up to 34% of the unwanted enantiomer) loss of optical purity in sensitive substrates such as hydroxyphenylglycine 1. This may be remedied using sodium succinate instead of sodium carbonate as base, but chemical yields are somewhat lower. Optically pure biaryl amino acids related to those found in the chloropeptins and vancomycin were synthesized by Suzuki coupling of 1 with indolylboronic acids 6-8 and with cyclic boronic acid 9.
• Synthesis of the Vancomycin CD and DE Ring Systems
  作者：Dale L. Boger、Robert M. Borzilleri、Seiji Nukui、Richard T. Beresis

  DOI：10.1021/jo970560p

  日期：1997.7.1

  Full details of the synthesis of the fully substituted vancomycin CD and DE ring systems are described and a potential solution to the control of the atropisomer stereochemistry is defined.
• Synthesis of Orthogonally Protected Actinoidic Acid Trimethyl Ether
  作者：Robert M. Williams、Yusuke Amino

  DOI：10.3987/com-18-s(f)2

  日期：——