benzyl (2S,3aS,6R,7S,7aR)-7-amino-2-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridine-1-carboxylate | 1002095-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: benzyl (2S,3aS,6R,7S,7aR)-7-amino-2-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridine-1-carboxylate
• 英文别名: benzyl (2S,3aS,6R,7S,7aR)-7-amino-2-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridine-1-carboxylate
• CAS: 1002095-39-7
• 化学式: C₃₅H₄₄N₄O₉S
• 分子量: 696.822
• InChiKey: SDOHLPIIEWTHJJ-HFHVEVKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  49
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  186
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3aS,6R,7S,7aR)-7-amino-2-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridine-1-carboxylate 、 苄氧基乙醛 在 4 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以75%的产率得到benzyl (1R,8R,10S,11R,13S,15S)-13-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6-hydroxy-3,5-dimethoxy-4-methyl-16-oxo-8-(phenylmethoxymethyl)-9,12,17-triazatetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-12-carboxylate
  参考文献：
  名称：

  An Efficient Synthetic Approach to Cyanocycline A and Bioxalomycin β2 via [C+NC+CC] Coupling

  摘要：

  The Ag-I catalyzed [C+NC+CC] coupling reaction of a 2,3-bisaminoaldehyde 5, L-glycyl sultam 6, and methyl acrylate provides highly functionalized pyrrolidine 7, the key intermediate in an efficient synthetic approach to the cyanocycline and bioxalomycin families of natural products. This powerful multicomponent reaction-based strategy reduces the number of steps needed to make these complex targets by more than one-third and paves the way for biological and biochemical evaluation of this natural product family.

  DOI：

  10.1021/ja077853c
• 作为产物：
  描述：

  benzyl (2S,3aS,6R,7S,7aR)-7-((tert-butoxycarbonyl)amino)-2-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-3H-3a,6-methanobenzo[c]isothiazole-1-carbonyl)-6-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-4-oxooctahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 benzyl (2S,3aS,6R,7S,7aR)-7-amino-2-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridine-1-carboxylate
  参考文献：
  名称：

  An Efficient Synthetic Approach to Cyanocycline A and Bioxalomycin β2 via [C+NC+CC] Coupling

  摘要：

  The Ag-I catalyzed [C+NC+CC] coupling reaction of a 2,3-bisaminoaldehyde 5, L-glycyl sultam 6, and methyl acrylate provides highly functionalized pyrrolidine 7, the key intermediate in an efficient synthetic approach to the cyanocycline and bioxalomycin families of natural products. This powerful multicomponent reaction-based strategy reduces the number of steps needed to make these complex targets by more than one-third and paves the way for biological and biochemical evaluation of this natural product family.

  DOI：

  10.1021/ja077853c

文献信息

• An Efficient Synthetic Approach to Cyanocycline A and Bioxalomycin β2 via [C+NC+CC] Coupling
  作者：H. Ümit Kaniskan、Philip Garner

  DOI：10.1021/ja077853c

  日期：2007.12.1

  The Ag-I catalyzed [C+NC+CC] coupling reaction of a 2,3-bisaminoaldehyde 5, L-glycyl sultam 6, and methyl acrylate provides highly functionalized pyrrolidine 7, the key intermediate in an efficient synthetic approach to the cyanocycline and bioxalomycin families of natural products. This powerful multicomponent reaction-based strategy reduces the number of steps needed to make these complex targets by more than one-third and paves the way for biological and biochemical evaluation of this natural product family.