phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside | 1492048-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 1492048-37-9
• 化学式: C₇₃H₈₁Cl₃N₄O₂₆S
• 分子量: 1568.88
• InChiKey: DOXBJZSSYZIKDI-LVDPQJHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.33
• 重原子数：
  107.0
• 可旋转键数：
  30.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  355.65
• 氢给体数：
  1.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A New Approach for the Synthesis of Hyperbranched N-Glycan Core Structures from Locust Bean Gum

  摘要：

  A novel protocol for the synthesis of general N-glycan core structures was established by means of Man beta(1 -> 4)Man peracetate derived from a naturally abundant locust bean gum as a key starting material. Phenyl (2-O-benzy1-4,6-O-benzylidine-beta-D-mannopyranosyl)-(1 -> 4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-beta-D-glucopyranoside facilitated the synthesis of key intermediates leading to hyperbranched N-glycan core structures.

  DOI：

  10.1021/ol403140h
• 作为产物：
  描述：

  phenyl (2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl)-(1 →4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside 、 O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)]-(1→2)-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl) trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A New Approach for the Synthesis of Hyperbranched N-Glycan Core Structures from Locust Bean Gum

  摘要：

  A novel protocol for the synthesis of general N-glycan core structures was established by means of Man beta(1 -> 4)Man peracetate derived from a naturally abundant locust bean gum as a key starting material. Phenyl (2-O-benzy1-4,6-O-benzylidine-beta-D-mannopyranosyl)-(1 -> 4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-beta-D-glucopyranoside facilitated the synthesis of key intermediates leading to hyperbranched N-glycan core structures.

  DOI：

  10.1021/ol403140h