(R)-N-[(R)-cyano-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]methyl]-4-methylbenzenesulfinamide | 203504-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-N-[(R)-cyano-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]methyl]-4-methylbenzenesulfinamide
• CAS: 203504-58-9
• 化学式: C₂₂H₂₈N₂O₄S
• 分子量: 416.541
• InChiKey: HZCOTSVAOODTQI-ADXZGYQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (R)-N-[(R)-cyano-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]methyl]-4-methylbenzenesulfinamide 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以76%的产率得到(R)-(-)-(3,5-diisopropoxy-4-methoxyphenyl)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-methoxy-3,5-diisopropyloxybenzaldehyde 在 异丙醇 、 lithium hexamethyldisilazane 作用下， 反应 0.25h， 生成 (R)-N-[(R)-cyano-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]methyl]-4-methylbenzenesulfinamide
  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