p-nosyl-L-Ser(3,4,6-tri-O-benzyl-α-D-GalNAc) o-allylbenzylamide | 1085337-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nosyl-L-Ser(3,4,6-tri-O-benzyl-α-D-GalNAc) o-allylbenzylamide
• 英文别名: (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-[(4-nitrophenyl)sulfonylamino]-N-[(2-prop-2-enylphenyl)methyl]propanamide
• CAS: 1085337-21-8
• 化学式: C₄₈H₅₂N₄O₁₁S
• 分子量: 893.027
• InChiKey: JALSSEVVBZWURE-PMPRZQJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  64
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  205
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  p-nosyl-L-Ser(3,4,6-tri-O-benzyl-α-D-GalNAc) o-allylbenzylamide 在 2,6-二甲基吡啶 、 四氧化锇 、 四丁基高碘酸铵 作用下， 以 水 、 丙酮 为溶剂， 反应 15.0h， 生成
  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-p-nosyl-L-aziridine-2-carboxamide 、 2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose 在 18-冠醚-6 、 potassium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 p-nosyl-L-Ser(3,4,6-tri-O-benzyl-β-D-GalNAc) o-allylbenzylamide 、 p-nosyl-L-Ser(3,4,6-tri-O-benzyl-α-D-GalNAc) 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

文献信息

• Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-<i>O</i>-Nucleophiles. Stereoselective Preparation of α- and β-<i>O</i>-Glycosyl Serine Conjugates
  作者：Daniel A. Ryan、David Y. Gin

  DOI：10.1021/ja804589j

  日期：2008.11.19

  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.