2-allyl 3,4-dimethyl 5-((S)-3-(3-((R)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate | 890139-51-2

• 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: 2-allyl 3,4-dimethyl 5-((S)-3-(3-((R)-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-enyl 5-[(3S)-3-[[(2R)-1-azido-3-phenylpropan-2-yl]carbamoylamino]-4-tri(propan-2-yl)silyloxybutyl]furan-2,3,4-tricarboxylate
• CAS: 890139-51-2
• 化学式: C₃₅H₅₁N₅O₉Si
• 分子量: 713.904
• InChiKey: NMZIHXCAXRHSJE-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  50
• 可旋转键数：
  23
• 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：

  2-allyl 3,4-dimethyl 5-((S)-3-(3-((R)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate 在 N-甲基吗啉 、 四(三苯基膦)钯 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2-{(S)-3-[3-((R)-1-Azidomethyl-2-phenyl-ethyl)-ureido]-4-triisopropylsilanyloxy-butyl}-5-(methyl-prop-2-ynyl-carbamoyl)-furan-3,4-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 allyl ester 在 辛酸铑 作用下， 以 苯 为溶剂， 反应 13.5h， 生成 2-allyl 3,4-dimethyl 5-((S)-3-(3-((R)-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.