bis(2-(2-methoxyethoxy)ethyl) (3-(2,5,8,11-tetraoxatridecan-13-yloxy)phenyl)phosphonite | 1337529-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: bis(2-(2-methoxyethoxy)ethyl) (3-(2,5,8,11-tetraoxatridecan-13-yloxy)phenyl)phosphonite
• 英文别名: Bis[2-(2-methoxyethoxy)ethoxy]-[3-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]phenyl]phosphane；bis[2-(2-methoxyethoxy)ethoxy]-[3-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]phenyl]phosphane
• CAS: 1337529-90-4
• 化学式: C₂₅H₄₅O₁₁P
• 分子量: 552.599
• InChiKey: VSFUFUOTCWMIPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  37
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  bis(2-(2-methoxyethoxy)ethyl) (3-(2,5,8,11-tetraoxatridecan-13-yloxy)phenyl)phosphonite 在 borane tetrahydrofurane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 以0.1653 g的产率得到bis(2-(2-methoxyethoxy)ethyl) (3-(2,5,8,11-tetraoxatridecan-13-yloxy)phenyl)phosphonite borane
  参考文献：
  名称：

  Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins

  摘要：

  Site-specific functionalization of proteins by bloorthogonal modification offers a convenient pathway to create, modify, and study biologically active biopolymers. In this paper the Staudinger reaction of aryl-phosphonites for the chemoselective functionalization of azido-peptides and proteins was probed. Different water-soluble phosphonites with ollgoethylene substituents were synthesized and reacted with unprotected azido-containing peptides in aqueous systems at room temperature in high conversions. Finally, the Staudinger-phosphonite reaction was successfully applied to the site-specific modification of the protein calmodulin.

  DOI：

  10.1021/ol2020175
• 作为产物：
  描述：

  2,5,8,11-四氧杂十三烷-13-基4-甲基苯磺酸酯 在 四氮唑 、 正丁基锂 、 potassium carbonate 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 37.0h， 生成 bis(2-(2-methoxyethoxy)ethyl) (3-(2,5,8,11-tetraoxatridecan-13-yloxy)phenyl)phosphonite
  参考文献：
  名称：

  Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins

  摘要：

  Site-specific functionalization of proteins by bloorthogonal modification offers a convenient pathway to create, modify, and study biologically active biopolymers. In this paper the Staudinger reaction of aryl-phosphonites for the chemoselective functionalization of azido-peptides and proteins was probed. Different water-soluble phosphonites with ollgoethylene substituents were synthesized and reacted with unprotected azido-containing peptides in aqueous systems at room temperature in high conversions. Finally, the Staudinger-phosphonite reaction was successfully applied to the site-specific modification of the protein calmodulin.

  DOI：

  10.1021/ol2020175

文献信息

• Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins
  作者：M. Robert J. Vallée、Paul Majkut、Ina Wilkening、Christoph Weise、Gregor Müller、Christian P. R. Hackenberger

  DOI：10.1021/ol2020175

  日期：2011.10.21

  Site-specific functionalization of proteins by bloorthogonal modification offers a convenient pathway to create, modify, and study biologically active biopolymers. In this paper the Staudinger reaction of aryl-phosphonites for the chemoselective functionalization of azido-peptides and proteins was probed. Different water-soluble phosphonites with ollgoethylene substituents were synthesized and reacted with unprotected azido-containing peptides in aqueous systems at room temperature in high conversions. Finally, the Staudinger-phosphonite reaction was successfully applied to the site-specific modification of the protein calmodulin.