(2S,4S)-3-<2-Azido-2-(4-methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone | 169176-61-8

• 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,4S)-3-<2-Azido-2-(4-methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(2S)-2-azido-2-(4-methoxyphenyl)acetyl]-4-benzyl-1,3-oxazolidin-2-one
• CAS: 169176-61-8
• 化学式: C₁₉H₁₈N₄O₄
• 分子量: 366.376
• InChiKey: YVDKUUHHKADZRM-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-3-<2-Azido-2-(4-methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 32.0h， 生成 (2R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-bromoethoxy)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
• 作为产物：
  描述：

  [2-(4-Methoxyphenyl)acetyl] 2,2-dimethylpropanoate 在 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 21.53h， 生成 (2S,4S)-3-<2-Azido-2-(4-methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone
  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

文献信息

• Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation
  作者：Anthony J. Pearson、Kieseung Lee

  DOI：10.1021/jo00127a020

  日期：1995.11

  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.