4-Methyl-benzenesulfinic acid [(R)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-amide | 203504-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Methyl-benzenesulfinic acid [(R)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-amide
• 英文别名: (R)-N-[(R)-cyano-(3,4,5-trimethoxyphenyl)methyl]-4-methylbenzenesulfinamide
• CAS: 203504-57-8
• 化学式: C₁₈H₂₀N₂O₄S
• 分子量: 360.434
• InChiKey: LHTXLQPNKIXONQ-ODCWNRFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  99.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-Methyl-benzenesulfinic acid [(R)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-amide 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (2S)-(+)-3,4,5-trimethoxyphenylglycine 、 (R)-(-)-(3,4,5-trimethoxyphenyl)glycine
  参考文献：
  名称：

  Sulfinimine-Mediated Asymmetric Synthesis of (R)-(4-Methoxy-3,5-dihydroxyphenyl)glycine:  The Central Amino Acid of Vancomycin and Related Agents

  摘要：

  The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, "EtAl(OR)CN", to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.

  DOI：

  10.1021/jo972076s
• 作为产物：
  描述：

  4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 在 异丙醇 、 lithium hexamethyldisilazane 作用下， 反应 0.25h， 生成 4-Methyl-benzenesulfinic acid [(R)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-amide
  参考文献：
  名称：

  Sulfinimine-Mediated Asymmetric Synthesis of (R)-(4-Methoxy-3,5-dihydroxyphenyl)glycine:  The Central Amino Acid of Vancomycin and Related Agents

  摘要：

  The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, "EtAl(OR)CN", to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.

  DOI：

  10.1021/jo972076s

文献信息

• Sulfinimine-Mediated Asymmetric Synthesis of (<i>R</i>)-(4-Methoxy-3,5-dihydroxyphenyl)glycine:  The Central Amino Acid of Vancomycin and Related Agents
  作者：Franklin A. Davis、Dean L. Fanelli

  DOI：10.1021/jo972076s

  日期：1998.3.1

  The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, "EtAl(OR)CN", to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.