N-(o-allylbenzyl)-1-p-nosyl-L-aziridine-2-carboxamide | 1085337-47-8

• 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: N-(o-allylbenzyl)-1-p-nosyl-L-aziridine-2-carboxamide
• 英文别名: pNs-Azy-NHABn
• CAS: 1085337-47-8
• 化学式: C₁₉H₁₉N₃O₅S
• 分子量: 401.443
• InChiKey: GWHXPEJXGQHNOR-YMXDCFFPSA-N

物化性质

• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(o-allylbenzyl)-1-p-nosyl-L-aziridine-2-carboxamide 、 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 在 三丁基膦 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 以78%的产率得到p-nosyl-L-Ser(3,4,6-tri-O-benzyl-β-D-GlcNAc) o-allylbenzylamide
  参考文献：
  名称：

  Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-O-Nucleophiles. Stereoselective Preparation of α- and β-O-Glycosyl Serine Conjugates

  摘要：

  The stereoselective formation of the alpha-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the alpha- or beta-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the B-GlcNAc-Ser and alpha-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation.

  DOI：

  10.1021/ja804589j
• 作为产物：
  描述：

  N-(o-allylbenzyl)-1-H-L-aziridine-2-carboxamide 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 以84%的产率得到N-(o-allylbenzyl)-1-p-nosyl-L-aziridine-2-carboxamide
  参考文献：
  名称：

  Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-O-Nucleophiles. Stereoselective Preparation of α- and β-O-Glycosyl Serine Conjugates

  摘要：

  The stereoselective formation of the alpha-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the alpha- or beta-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the B-GlcNAc-Ser and alpha-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation.

  DOI：

  10.1021/ja804589j