2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride | 1492048-09-5

• 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: 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride
• CAS: 1492048-09-5
• 化学式: C₂₄H₃₂ClN₃O₁₅
• 分子量: 637.982
• InChiKey: FNVCTOKORTURCA-MNXGPZKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  234.25
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride 、 苯硫酚 在 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 重水 、 乙酸乙酯 为溶剂， 以47%的产率得到phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-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：

  2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-acetyl-D-glucal 在 sodium azide 、 ammonium cerium (IV) nitrate 、 四乙基氯化铵 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride
  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