methyl (8S,11R)-11-benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylate | 168292-12-4

• 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: methyl (8S,11R)-11-benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylate
• CAS: 168292-12-4
• 化学式: C₂₇H₂₅N₃O₈
• 分子量: 519.511
• InChiKey: RELZNOOAYBQOAX-RDGATRHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (8S,11R)-11-benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到methyl (8S,11R)-16-amino-11-benzyl-5-methoxy-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylate
  参考文献：
  名称：

  A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

  摘要：

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

  DOI：

  10.1021/jo00125a026
• 作为产物：
  描述：

  甲基3-氟苯酚乙酯 在 盐酸 、 18-冠醚-6 、 硫酸 、 硝酸 、 三溴化硼 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.12h， 生成 methyl (8S,11R)-11-benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylate
  参考文献：
  名称：

  A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

  摘要：

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

  DOI：

  10.1021/jo00125a026

文献信息

• A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
  作者：Jieping Zhu、Rene Beugelmans、Sebastien Bourdet、Jacqueline Chastanet、George Roussi

  DOI：10.1021/jo00125a026

  日期：1995.10

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.