N-<2(R)-Azido-2-<3-(benzyloxy)-4-methoxyphenyl>acetyl>-D-phenylalanine (methoxyethoxy)methyl ester | 159579-65-4

• 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: N-<2(R)-Azido-2-<3-(benzyloxy)-4-methoxyphenyl>acetyl>-D-phenylalanine (methoxyethoxy)methyl ester
• 英文别名: 2-methoxyethoxymethyl (2R)-2-[[(2R)-2-azido-2-(4-methoxy-3-phenylmethoxyphenyl)acetyl]amino]-3-phenylpropanoate
• CAS: 159579-65-4
• 化学式: C₂₉H₃₂N₄O₇
• 分子量: 548.596
• InChiKey: YIAJUZOZSOONTG-SHQCIBLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-<2(R)-Azido-2-<3-(benzyloxy)-4-methoxyphenyl>acetyl>-D-phenylalanine (methoxyethoxy)methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 <3-<<2-Methyl-3-methoxy-5-<4(R)-isopropyl-3,6-dimethoxy-1,4-dihydropyrazinyl>phenyl>oxy>-N-(tert-butoxycarbonyl)-(R)-4-methoxyphenylglycinyl>-D-phenylalanine (methoxyethoxy)methyl ester
  参考文献：
  名称：

  Synthesis of a 14-Membered Cyclic Peptide Model of the CFG Rings of Ristocetin A and Observations on Atropdiastereoisomerism

  摘要：

  Two routes for the synthesis of a 14-membered heterodetic cyclic peptide as a model for the CFG ring system of the antibiotic ristocetin A (2) are described. The key aryl ether bonds for this molecule were constructed by using the reaction of phenoxides from (hydroxyaryl)glycine derivatives with tricarbonyl (3-methoxy-2-methylchlorobenzene) manganese hexafluorophosphate (11). This coupling reaction can be performed in the presence of protected amino acids and dipeptides without racemization of the sensitive arylglycine. Stereoselective introduction of the F-ring glycine side chain was accomplished by reaction of the aryl ether manganese complexes with Schollkopf's bislactim glycine enolate equivalent. The product(s) from this reaction were demetalated and aromatized by treatment with N-bromosuccinimide. Deprotection of the aromatized compounds followed by cycloamidation furnished two atrodiastereomeric cyclic peptides corresponding to the target molecule, the structures of which were assigned on the basis of BD-NMR NOESY experiments coupled with molecular modeling. One of the product molecules corresponds closely to the structure that has been proposed for the CFG ring system of proposed for the CFG ring of ristocetin, except for the orientation of the w(3) amide group.

  DOI：

  10.1021/jo00088a010
• 作为产物：
  描述：

  D-苯丙氨酸 在 palladium on activated charcoal 氢气 、 四丁基碘化铵 、 sodium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.88h， 生成 N-<2(R)-Azido-2-<3-(benzyloxy)-4-methoxyphenyl>acetyl>-D-phenylalanine (methoxyethoxy)methyl ester
  参考文献：
  名称：

  Synthesis of a 14-Membered Cyclic Peptide Model of the CFG Rings of Ristocetin A and Observations on Atropdiastereoisomerism

  摘要：

  Two routes for the synthesis of a 14-membered heterodetic cyclic peptide as a model for the CFG ring system of the antibiotic ristocetin A (2) are described. The key aryl ether bonds for this molecule were constructed by using the reaction of phenoxides from (hydroxyaryl)glycine derivatives with tricarbonyl (3-methoxy-2-methylchlorobenzene) manganese hexafluorophosphate (11). This coupling reaction can be performed in the presence of protected amino acids and dipeptides without racemization of the sensitive arylglycine. Stereoselective introduction of the F-ring glycine side chain was accomplished by reaction of the aryl ether manganese complexes with Schollkopf's bislactim glycine enolate equivalent. The product(s) from this reaction were demetalated and aromatized by treatment with N-bromosuccinimide. Deprotection of the aromatized compounds followed by cycloamidation furnished two atrodiastereomeric cyclic peptides corresponding to the target molecule, the structures of which were assigned on the basis of BD-NMR NOESY experiments coupled with molecular modeling. One of the product molecules corresponds closely to the structure that has been proposed for the CFG ring system of proposed for the CFG ring of ristocetin, except for the orientation of the w(3) amide group.

  DOI：

  10.1021/jo00088a010

文献信息

• Synthesis of a 14-Membered Cyclic Peptide Model of the CFG Rings of Ristocetin A and Observations on Atropdiastereoisomerism
  作者：Anthony J. Pearson、Hunwoo Shin

  DOI：10.1021/jo00088a010

  日期：1994.5

  Two routes for the synthesis of a 14-membered heterodetic cyclic peptide as a model for the CFG ring system of the antibiotic ristocetin A (2) are described. The key aryl ether bonds for this molecule were constructed by using the reaction of phenoxides from (hydroxyaryl)glycine derivatives with tricarbonyl (3-methoxy-2-methylchlorobenzene) manganese hexafluorophosphate (11). This coupling reaction can be performed in the presence of protected amino acids and dipeptides without racemization of the sensitive arylglycine. Stereoselective introduction of the F-ring glycine side chain was accomplished by reaction of the aryl ether manganese complexes with Schollkopf's bislactim glycine enolate equivalent. The product(s) from this reaction were demetalated and aromatized by treatment with N-bromosuccinimide. Deprotection of the aromatized compounds followed by cycloamidation furnished two atrodiastereomeric cyclic peptides corresponding to the target molecule, the structures of which were assigned on the basis of BD-NMR NOESY experiments coupled with molecular modeling. One of the product molecules corresponds closely to the structure that has been proposed for the CFG ring system of proposed for the CFG ring of ristocetin, except for the orientation of the w(3) amide group.