2-diphenylphosphino-N-acetylimidazole | 289884-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-diphenylphosphino-N-acetylimidazole
• 英文别名: 1-(2-Diphenylphosphanylimidazol-1-yl)ethanone
• CAS: 289884-69-1
• 化学式: C₁₇H₁₅N₂OP
• 分子量: 294.293
• InChiKey: YSEWKRNJWMCLIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-diphenylphosphino-N-acetylimidazole 、 2,3,4-tri-O-benzyl-α-L-fucopyranosyl azide 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-acetamido-2,3,4-tri-O-benzyl-α-L-fucopyranose 、 1-acetamido-2,3,4-tri-O-benzyl-β-L-fucopyranose
  参考文献：
  名称：

  Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides

  摘要：

  alpha-Glycosyl azides can be transformed into the corresponding alpha-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The of alpha-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.159
• 作为产物：
  描述：

  2-(diphenylphosphino)-1-(diethoxymethyl)imidazole 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 以 丙酮 为溶剂， 生成 2-diphenylphosphino-N-acetylimidazole
  参考文献：
  名称：

  “无痕”施陶丁格连接，用于酰胺键的化学选择性合成。

  摘要：

  [反应：见正文]在这里，我们报告了对我们先前报道的“斯托丁格连接”的一种新颖修饰，该修饰从叠氮化物和经过特殊功能化的膦生成酰胺键。不需要远端官能团的正交保护的这种选择性形成酰胺键的方法应该在合成和生物化学中找到通用的用途。

  DOI：

  10.1021/ol006054v

文献信息

• WATER-SOLUBLE PHOSPHINOTHIOL REAGENTS
  申请人：Raines Ronald T.

  公开号：US20100048866A1

  公开（公告）日：2010-02-25

  Water soluble reagents and methods for the formation of an amide bond between a phosphinothioester and an azide in an aqueous medium. The phosphinothioester is generated using a water-soluble phosphinothiol reagent. This reaction allows formation of an amide bond between a wide variety of chemical species including amino acids, peptides or protein fragments in an aqueous solution. Of particular interest, this reaction allows for the formation of an amide bond in a physiological setting. In a specific embodiment, this invention provides reagents and methods for peptide ligation in an aqueous medium. The reaction eliminates the need for a cysteine residue and is traceless leaving no residual atoms in the ligated peptide product.
• US7256259B2
  申请人：——

  公开号：US7256259B2

  公开（公告）日：2007-08-14
• US8410247B2
  申请人：——

  公开号：US8410247B2

  公开（公告）日：2013-04-02
• A “Traceless” Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds
  作者：Eliana Saxon、Joshua I. Armstrong、Carolyn R. Bertozzi

  DOI：10.1021/ol006054v

  日期：2000.7.1

  [reaction: see text] Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine. This method for the selective formation of an amide bond, which does not require the orthogonal protection of distal functional groups, should find general utility in synthetic and biological chemistry.

  [反应：见正文]在这里，我们报告了对我们先前报道的“斯托丁格连接”的一种新颖修饰，该修饰从叠氮化物和经过特殊功能化的膦生成酰胺键。不需要远端官能团的正交保护的这种选择性形成酰胺键的方法应该在合成和生物化学中找到通用的用途。
• Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides
  作者：Aldo Bianchi、Anna Bernardi

  DOI：10.1016/j.tetlet.2003.12.159

  日期：2004.3

  alpha-Glycosyl azides can be transformed into the corresponding alpha-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The of alpha-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process. (C) 2004 Elsevier Ltd. All rights reserved.