4-(((1R,2R)-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)-1-((2R,3S,4S,5R,6R)-6-(methylthio)-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)propan-2-yl)oxy)-4-oxobutanoic acid | 1630970-36-3

• 英文名称: 4-(((1R,2R)-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)-1-((2R,3S,4S,5R,6R)-6-(methylthio)-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)propan-2-yl)oxy)-4-oxobutanoic acid
• CAS: 1630970-36-3
• 化学式: C₃₁H₆₂N₂O₉SSi₃
• 分子量: 723.164
• InChiKey: XQZMSLGXWWKUSZ-ZAPKNVLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  132.86
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-(((1R,2R)-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)-1-((2R,3S,4S,5R,6R)-6-(methylthio)-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)propan-2-yl)oxy)-4-oxobutanoic acid 、 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(1R,2R)-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)-1-((2R,3S,4S,5R,6R)-6-(methylthio)-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)propan-2-yl 1-(3-amino-4-(methoxycarbonyl)phenyl)-1,17-dioxo-6,9,12-trioxa-2,16-diazaicosan-20-oate
  参考文献：
  名称：

  Amine-Selective Bioconjugation Using Arene Diazonium Salts

  摘要：

  A novel bioconjugation strategy is presented that relies on the coupling of diazonium terephthalates with amines in proteins. The diazonium captures the amine while the vicinal ester locks it through cyclization, ensuring no reversibility. The reaction is highly efficient and proceeds under mild conditions and short reaction times. Densely functionalized, complex natural products were directly coupled to proteins using low concentrations of coupling partners.

  DOI：

  10.1021/ol5016509
• 作为产物：
  描述：

  丁二酸酐 、 2,3,4-三-O-三甲基硅烷基林可霉素 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.25h， 以49%的产率得到4-(((1R,2R)-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)-1-((2R,3S,4S,5R,6R)-6-(methylthio)-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)propan-2-yl)oxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Amine-Selective Bioconjugation Using Arene Diazonium Salts

  摘要：

  A novel bioconjugation strategy is presented that relies on the coupling of diazonium terephthalates with amines in proteins. The diazonium captures the amine while the vicinal ester locks it through cyclization, ensuring no reversibility. The reaction is highly efficient and proceeds under mild conditions and short reaction times. Densely functionalized, complex natural products were directly coupled to proteins using low concentrations of coupling partners.

  DOI：

  10.1021/ol5016509