(2R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-iodoethoxy)propyl>phenoxy>-4-methoxy-N--L-(4-methoxyphenyl)glycinyl>-D-phenylglycine ethyl ester | 169176-65-2

• 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: (2R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-iodoethoxy)propyl>phenoxy>-4-methoxy-N--L-(4-methoxyphenyl)glycinyl>-D-phenylglycine ethyl ester
• 英文别名: 2-iodoethyl (2R)-3-[4-[5-[(1R)-2-ethoxy-1-[[(2S)-2-(4-methoxyphenyl)-2-(phenylmethoxycarbonylamino)acetyl]amino]-2-oxoethyl]-2-methoxyphenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 169176-65-2
• 化学式: C₄₄H₅₀IN₃O₁₂
• 分子量: 939.798
• InChiKey: UJQCMPZPCNPIJA-CRXACVATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  60
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  186
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-iodoethoxy)propyl>phenoxy>-4-methoxy-N--L-(4-methoxyphenyl)glycinyl>-D-phenylglycine ethyl ester 在 palladium on activated charcoal N,N-二甲基丙烯基脲 、 samarium diiodide 、 五氟苯基二苯基磷酸酯 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 30.08h， 生成 ethyl (8R,11S,14R)-4-methoxy-11-(4-methoxyphenyl)-14-[(2-methylpropan-2-yl)oxycarbonylamino]-10,13-dioxo-2-oxa-9,12-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-8-carboxylate
  参考文献：
  名称：

  Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation

  摘要：

  A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described. A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues. Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.

  DOI：

  10.1021/jo00127a020
• 作为产物：
  描述：

  (2R)-2-Azido-2-<(3-(benzyloxy)-4-methoxy)phenyl>acetic acid 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 57.0h， 生成 (2R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-iodoethoxy)propyl>phenoxy>-4-methoxy-N--L-(4-methoxyphenyl)glycinyl>-D-phenylglycine ethyl ester
  参考文献：
  名称：

  Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation

  摘要：

  A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described. A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues. Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.

  DOI：

  10.1021/jo00127a020