D-N-<(1,1-dimethylethoxy)carbonyl>-O--2-oxo-2-ethoxyethyl>phenyl>tyrosine | 139377-44-9

• 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: D-N-<(1,1-dimethylethoxy)carbonyl>-O--2-oxo-2-ethoxyethyl>phenyl>tyrosine
• 英文别名: D-N-[(1,1-dimethylethoxy)carbonyl]-O-(D-3-{1-[N-(2-aminoacetyl)amino]-2-oxo-2-ethoxyethyl}phenyl)tyrosine；(2R)-3-[4-[3-[(1R)-1-[(2-aminoacetyl)amino]-2-ethoxy-2-oxoethyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 139377-44-9
• 化学式: C₂₆H₃₃N₃O₈
• 分子量: 515.563
• InChiKey: YAHOZYRIYHJQGK-IFMALSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  166.28
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  D-N-<(1,1-dimethylethoxy)carbonyl>-4-D-<3-<1-acetyl>amino>-2-oxo-2-ethoxyethyl>phenoxy>phenylalanine 2-bromoethyl ester 在 palladium on activated charcoal 1,3-环己二烯 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 D-N-<(1,1-dimethylethoxy)carbonyl>-O--2-oxo-2-ethoxyethyl>phenyl>tyrosine
  参考文献：
  名称：

  Model studies on the synthesis of carboxylate-binding pocket analogs of vancomycin using arene-ruthenium chemistry

  摘要：

  Preparation of several protected (D)-chlorophenylalanine derivatives in high optical purity and their complex formation with the [RuCp]+ moiety are described. The complexation reaction, as well as subsequent photochemical decomplexations, proceeds with retention of optical purity. Reactions of these chloroarene complexes with 3-hydroxyphenylglycine derivatives proceed under mild conditions to give aryl ether-ruthenium complexes, which can be converted to diaryl ethers in which both aromatic rings have protected amino acid or peptide side chains. Efforts to effect cycloamidation to give vancomycin carboxylate-binding pocket analogues, using a number of known coupling reagents, were unsuccessful.

  DOI：

  10.1021/jo00032a028