(2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 1-methyl ester | 600709-00-0

• 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: (2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 1-methyl ester
• 英文别名: (4R,5S)-6-methoxy-5-(methoxycarbonylamino)-4-(4-methoxyphenyl)-6-oxohexanoic acid
• CAS: 600709-00-0
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: GKQPFUZMAJXJDP-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 1-methyl ester 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二硫化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 (1R,9R,12S)-5-methoxy-8-oxo-11-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-12-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of a New Conformation-Constrained l-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands

  摘要：

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.

  DOI：

  10.1021/jo0340152
• 作为产物：
  描述：

  (2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 6-tert-butyl ester 1-methyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 1-methyl ester
  参考文献：
  名称：

  Synthesis of a New Conformation-Constrained l-Tyrosine Analogue as a Potential Scaffold for SH2 Domain Ligands

  摘要：

  The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having chi(1) and chi(2) angles constrained to values observed for a phosp(h)otyrosyl (pTyr) residue bound to the p56(lck) SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.

  DOI：

  10.1021/jo0340152