methyl(R)-N-Boc-(3-(2,4-dimethoxy-6-hydroxymethylphenyl)-4-methoxyphenyl)glycinate | 928765-31-5

• 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-(2,4-dimethoxy-6-hydroxymethylphenyl)-4-methoxyphenyl)glycinate
• 英文别名: methyl (2R)-2-[3-[2-(hydroxymethyl)-4,6-dimethoxyphenyl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 928765-31-5
• 化学式: C₂₄H₃₁NO₈
• 分子量: 461.512
• InChiKey: MWMFQKKGZOSHNL-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl(R)-N-Boc-(3-(2,4-dimethoxy-6-hydroxymethylphenyl)-4-methoxyphenyl)glycinate 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 methyl (2R)-2-[3-[2,4-dimethoxy-6-(phenylmethoxycarbonylaminomethyl)phenyl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
  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
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 palladium diacetate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 盐酸 、 正丁基锂 、 水 、 sodium carbonate 作用下， 以 甲醇 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 18.0h， 生成 methyl(R)-N-Boc-(3-(2,4-dimethoxy-6-hydroxymethylphenyl)-4-methoxyphenyl)glycinate
  参考文献：
  名称：

  Total Synthesis of Vancomycin—Part 1: Design and Development of Methodology

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990903)5:9<2584::aid-chem2584>3.0.co;2-b

文献信息

• 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.
• Total Synthesis of Vancomycin—Part 1: Design and Development of Methodology
  作者：K. C. Nicolaou、Hui Li、Christopher N. C. Boddy、Joshi M. Ramanjulu、Tai-Yuen Yue、Swaminathan Natarajan、Xin-Jie Chu、Stefan Bräse、Frank Rübsam

  DOI：10.1002/(sici)1521-3765(19990903)5:9<2584::aid-chem2584>3.0.co;2-b

  日期：1999.9.3