(2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid | 139517-62-7

• 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: (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• 英文别名: (R)-2-(3-bromo-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino)acetic acid；N-tert-butoxycarbonyl-(R)-3-bromo-4-hydroxyphenylglycine；(R)-N-Boc-3-bromo-4-hydroxyphenylglycine
• CAS: 139517-62-7
• 化学式: C₁₃H₁₆BrNO₅
• 分子量: 346.178
• InChiKey: UYHAGBGUYCTQPD-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 0.25h， 生成 methyl (R)-N-Boc-3-bromo-4-methoxyphenylglycinate
  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：

  D(-)-对羟基苯甘氨酸 在 sodium hydroxide 、 溴 作用下， 以 溶剂黄146 、 叔丁醇 为溶剂， 反应 25.0h， 生成 (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
  参考文献：
  名称：

  Racemization in Suzuki Couplings: A Quantitative Study Using 4-Hydroxyphenylglycine and Tyrosine Derivatives as Probe Molecules

  摘要：

  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.

  DOI：

  10.1021/jo0621266

文献信息

• Synthesis of Simplified Halogenated Chondramide Derivatives with Strong Cytostatic Properties
  作者：Dominic Becker、Uli Kazmaier

  DOI：10.1002/ejoc.201403577

  日期：2015.4

  in the cytotoxicity of these interesting depsipeptides. This effect can be almost compensated for by introduction of a second chlorine atom on the β-tyrosine moiety of the natural products. These simplified chondramides are much easier accessible than natural chondramides.

  从软骨酰胺的 ω-羟基酸中去除甲基和立体中心会导致这些有趣的缩肽的细胞毒性显着下降。这种影响几乎可以通过在天然产物的 β-酪氨酸部分引入第二个氯原子来补偿。这些简化的软骨素比天然软骨素更容易获得。
• Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite <i>Plasmodium falciparum</i> and Optimization Efforts
  作者：Claire Le Manach、Jean Dam、John G. Woodland、Gurminder Kaur、Lutete P. Khonde、Christel Brunschwig、Mathew Njoroge、Kathryn J. Wicht、André Horatscheck、Tanya Paquet、Grant A. Boyle、Liezl Gibhard、Dale Taylor、Nina Lawrence、Tomas Yeo、Sachel Mok、Richard T. Eastman、Dorjbal Dorjsuren、Daniel C. Talley、Hui Guo、Anton Simeonov、Janette Reader、Mariëtte van der Watt、Erica Erlank、Nelius Venter、Jacek W. Zawada、Ayesha Aswat、Luisa Nardini、Theresa L. Coetzer、Sonja B. Lauterbach、Belinda C. Bezuidenhout、Anjo Theron、Dalu Mancama、Lizette L. Koekemoer、Lyn-Marie Birkholtz、Sergio Wittlin、Michael Delves、Sabine Ottilie、Elizabeth A. Winzeler、Thomas W. von Geldern、Dennis Smith、David A. Fidock、Leslie J. Street、Gregory S. Basarab、James Duffy、Kelly Chibale

  DOI：10.1021/acs.jmedchem.1c00034

  日期：2021.2.25
• Brown, Allan G.; Crimmin, Michael J.; Edwards, Peter D., Journal of the Chemical Society. Perkin transactions I, 1992, # 1, p. 123 - 130
  作者：Brown, Allan G.、Crimmin, Michael J.、Edwards, Peter D.

  DOI：——

  日期：——
• 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.