(S)-3-{7-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-benzofuran-5-yl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester | 865692-01-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S)-3-{7-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-benzofuran-5-yl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester
• 英文别名: methyl (2S)-3-[4-[[5-[(2S)-3-methoxy-3-oxo-2-[(2,2,2-trifluoroacetyl)amino]propyl]-1-benzofuran-7-yl]oxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 865692-01-9
• 化学式: C₂₉H₃₁F₃N₂O₉
• 分子量: 608.568
• InChiKey: MAZSFAUZHCWKBW-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-3-{7-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-benzofuran-5-yl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester 在 盐酸 、 PPh₃RhCl 、 potassium carbonate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.17h， 生成 (S,S)-isodityrosine bis hydrochloride
  参考文献：
  名称：

  Synthesis of (S,S)-Isodityrosine by Dötz Benzannulation

  摘要：

  A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dotz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.

  DOI：

  10.1021/jo050363n
• 作为产物：
  描述：

  (R)-N-叔丁氧羰基-3-碘代丙氨酸甲酯 在 palladium diacetate 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 甲酸 、 chlorotrimethylsilyl chloride 、 四丁基氟化铵 、 1,2-二溴乙烷 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (S)-3-{7-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-benzofuran-5-yl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of (S,S)-Isodityrosine by Dötz Benzannulation

  摘要：

  A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dotz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.

  DOI：

  10.1021/jo050363n

文献信息

• Synthesis of (<i>S</i>,<i>S</i>)-Isodityrosine by Dötz Benzannulation
  作者：Anuradha Gupta、Subhabrata Sen、Michael Harmata、Shon R. Pulley

  DOI：10.1021/jo050363n

  日期：2005.9.1

  A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dotz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.