p-nosyl-L-Ser(2,3,4,6-tetra-O-benzyl-β-D-Gal-(1->3)-4,6-di-O-isopropylidene-α-D-GalNAc) o-allylbenzylamide | 1085337-23-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-nosyl-L-Ser(2,3,4,6-tetra-O-benzyl-β-D-Gal-(1->3)-4,6-di-O-isopropylidene-α-D-GalNAc) o-allylbenzylamide
• 英文别名: (2S)-3-[[(4aR,6S,7R,8R,8aR)-7-acetamido-2,2-dimethyl-8-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[(4-nitrophenyl)sulfonylamino]-N-[(2-prop-2-enylphenyl)methyl]propanamide
• CAS: 1085337-23-0
• 化学式: C₆₄H₇₂N₄O₁₆S
• 分子量: 1185.36
• InChiKey: FVTVAPFWTSNTLW-KQZIMGLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  251
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  N-(o-allylbenzyl)-1-p-nosyl-L-aziridine-2-carboxamide 、 tetra-O-benzyl-β-D-galactopyranose-(1->3)-2-acetamido-2-deoxy-4,6-di-O-isopropylidene-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(2,3,4,6-tetra-O-benzyl-β-D-Gal-(1->3)-4,6-di-O-isopropylidene-β-D-GalNAc) o-allylbenzylamide 、 p-nosyl-L-Ser(2,3,4,6-tetra-O-benzyl-β-D-Gal-(1->3)-4,6-di-O-isopropylidene-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.