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 | 1492048-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: TrocNH(-2d)Glc3Ac4Ac6Ac(b1-2)[TrocNH(-2d)Glc3Ac4Ac6Ac(b1-4)]Man3Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-4-acetyloxy-3,5-bis[[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 1492048-36-8
• 化学式: C₄₂H₅₂Cl₉N₃O₂₆
• 分子量: 1333.96
• InChiKey: BNLRQYZOXQWDHD-APJIMDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  80
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  366
• 氢给体数：
  3
• 氢受体数：
  27

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：

  {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)]}-1,3,6-tri-O-acetyl-D-mannopyranose 在 一水合肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 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
  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