2-(trimethylsilyl)ethyl (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoate | 208448-25-3

• 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: 2-(trimethylsilyl)ethyl (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoate
• 英文别名: 2-trimethylsilylethyl (2R)-2-azido-2-[4-methoxy-3,5-bis(phenylmethoxy)phenyl]acetate
• CAS: 208448-25-3
• 化学式: C₂₈H₃₃N₃O₅Si
• 分子量: 519.673
• InChiKey: YNVJPYVNPILXII-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoate 在 palladium on activated charcoal 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 胸苷酸 、 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 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 2-(trimethylsilyl)ethyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate
  参考文献：
  名称：

  Synthesis of a Model Bicyclic CDE Ring System of Ristocetin A and Observation of a Facile Inversion of Configuration in a 16-Membered DE Ring Model

  摘要：

  Areneruthenium chemistry was used to effect intramolecular SNAr reactions between phenoxide nucleophiles and chlorophenylalanine residues that are connected by a peptide chain, resulting in the construction of a bicyclic peptide aryl ether system that corresponds to the BCDF system of the glycopeptide antibiotics ristocetin A and teicoplanin. A facile and selective base-catalyzed complete inversion of configuration at the D ring arylglycine residue was observed when this unit is the carboxylate terminus on a 16-membered ring system corresponding to the DEF rings of the target molecules. The inversion appears to result from an overwhelming thermodynamic preference for the inverted system and is supported by molecular mechanics and semiempirical calculations on the minimized conformations of the epimeric molecules.

  DOI：

  10.1021/jo980060b
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以96%的产率得到2-(trimethylsilyl)ethyl (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoate
  参考文献：
  名称：

  Synthesis of a Model Bicyclic CDE Ring System of Ristocetin A and Observation of a Facile Inversion of Configuration in a 16-Membered DE Ring Model

  摘要：

  Areneruthenium chemistry was used to effect intramolecular SNAr reactions between phenoxide nucleophiles and chlorophenylalanine residues that are connected by a peptide chain, resulting in the construction of a bicyclic peptide aryl ether system that corresponds to the BCDF system of the glycopeptide antibiotics ristocetin A and teicoplanin. A facile and selective base-catalyzed complete inversion of configuration at the D ring arylglycine residue was observed when this unit is the carboxylate terminus on a 16-membered ring system corresponding to the DEF rings of the target molecules. The inversion appears to result from an overwhelming thermodynamic preference for the inverted system and is supported by molecular mechanics and semiempirical calculations on the minimized conformations of the epimeric molecules.

  DOI：

  10.1021/jo980060b

文献信息

• Synthesis of a Model Bicyclic CDE Ring System of Ristocetin A and Observation of a Facile Inversion of Configuration in a 16-Membered DE Ring Model
  作者：Anthony J. Pearson、Mariappan V. Chelliah

  DOI：10.1021/jo980060b

  日期：1998.5.1

  Areneruthenium chemistry was used to effect intramolecular SNAr reactions between phenoxide nucleophiles and chlorophenylalanine residues that are connected by a peptide chain, resulting in the construction of a bicyclic peptide aryl ether system that corresponds to the BCDF system of the glycopeptide antibiotics ristocetin A and teicoplanin. A facile and selective base-catalyzed complete inversion of configuration at the D ring arylglycine residue was observed when this unit is the carboxylate terminus on a 16-membered ring system corresponding to the DEF rings of the target molecules. The inversion appears to result from an overwhelming thermodynamic preference for the inverted system and is supported by molecular mechanics and semiempirical calculations on the minimized conformations of the epimeric molecules.