3,4-dimethyl 2-prop-2-ynyl 5-((S)-3-(3-((S)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate | 890139-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dimethyl 2-prop-2-ynyl 5-((S)-3-(3-((S)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate
• 英文别名: 3-O,4-O-dimethyl 2-O-prop-2-ynyl 5-[(3S)-3-[[(2S)-1-azido-3-phenylpropan-2-yl]carbamoylamino]-4-tri(propan-2-yl)silyloxybutyl]furan-2,3,4-tricarboxylate
• CAS: 890139-50-1
• 化学式: C₃₅H₄₉N₅O₉Si
• 分子量: 711.888
• InChiKey: ABRMRHNGMSSRIJ-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl 2-prop-2-ynyl 5-((S)-3-(3-((S)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到(10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1(19),5(21),6,17-tetraene-18,19-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Macrocycloadditions Leading to Conformationally Restricted Small Molecules

  摘要：

  The Cu(I)-catalyzed cycloaddition of alkynes and azides (click reaction) provides a robust method for the construction of macrocyclic small molecules via an intramolecular macrocycloaddition. A three-subunit system has been used to explore the tolerance of this macrocycloaddition to variations of stereochemistries and substituents.

  DOI：

  10.1021/ol0604724
• 作为产物：
  描述：

  2-Diazo-3-oxo-3-((S)-2-oxo-5-triisopropylsilanyloxymethyl-pyrrolidin-1-yl)-propionic acid prop-2-ynyl ester 在 辛酸铑 作用下， 以 苯 为溶剂， 反应 13.5h， 生成 3,4-dimethyl 2-prop-2-ynyl 5-((S)-3-(3-((S)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate
  参考文献：
  名称：

  Macrocycloadditions Leading to Conformationally Restricted Small Molecules

  摘要：

  The Cu(I)-catalyzed cycloaddition of alkynes and azides (click reaction) provides a robust method for the construction of macrocyclic small molecules via an intramolecular macrocycloaddition. A three-subunit system has been used to explore the tolerance of this macrocycloaddition to variations of stereochemistries and substituents.

  DOI：

  10.1021/ol0604724

文献信息

• Macrocycloadditions Leading to Conformationally Restricted Small Molecules
  作者：Ryan E. Looper、Daniela Pizzirani、Stuart L. Schreiber

  DOI：10.1021/ol0604724

  日期：2006.5.1

  The Cu(I)-catalyzed cycloaddition of alkynes and azides (click reaction) provides a robust method for the construction of macrocyclic small molecules via an intramolecular macrocycloaddition. A three-subunit system has been used to explore the tolerance of this macrocycloaddition to variations of stereochemistries and substituents.