(S)-3-{4-benzyloxy-3-[4-((S)-2-dibenzylamino-2-methoxycarbonylethyl)phenoxy]phenyl}-2-(tritylamino)propionic acid benzyl ester | 903523-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-3-{4-benzyloxy-3-[4-((S)-2-dibenzylamino-2-methoxycarbonylethyl)phenoxy]phenyl}-2-(tritylamino)propionic acid benzyl ester
• 英文别名: methyl (2S)-2-(dibenzylamino)-3-[4-[5-[(2S)-3-oxo-3-phenylmethoxy-2-(tritylamino)propyl]-2-phenylmethoxyphenoxy]phenyl]propanoate
• CAS: 903523-84-2
• 化学式: C₆₆H₆₀N₂O₆
• 分子量: 977.212
• InChiKey: OPLRYBNTUJCSQZ-OBXNHJGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  74
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-3-{4-benzyloxy-3-[4-((S)-2-dibenzylamino-2-methoxycarbonylethyl)phenoxy]phenyl}-2-(tritylamino)propionic acid benzyl ester 在 palladium on activated charcoal lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 二苯基磷酸 、 氢气 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 136.5h， 生成 K-13
  参考文献：
  名称：

  Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives

  摘要：

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.

  DOI：

  10.1021/jo0606960
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 caesium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (S)-3-{4-benzyloxy-3-[4-((S)-2-dibenzylamino-2-methoxycarbonylethyl)phenoxy]phenyl}-2-(tritylamino)propionic acid benzyl ester
  参考文献：
  名称：

  Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives

  摘要：

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.

  DOI：

  10.1021/jo0606960