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 | 1492048-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: (2R,4aR,6S,7S,8S,8aS)-6-[(2R,3S,4R,5R,6S)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 1492048-21-1
• 化学式: C₄₆H₄₇N₃O₉S
• 分子量: 817.96
• InChiKey: IDQKMPNXZZPFDP-UMJFWBOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  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-{O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→4)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以69%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-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→4)-3,6-di-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
• 作为产物：
  描述：

  phenyl (2,3:4,6-di-O-benzylidine-β-D-mannopyranosyl)-(1→4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以68%的产率得到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
  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