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-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside | 1492048-42-6

• 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-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-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-4-acetyloxy-6-[(2S,3S,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-phenylmethoxyoxan-4-yl]oxy-3,5-bis[[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 1492048-42-6
• 化学式: C₇₉H₉₃Cl₆N₅O₃₄S
• 分子量: 1901.4
• InChiKey: YBMODVKVYFNAAZ-VEVJTVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  125
• 可旋转键数：
  47
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  478
• 氢给体数：
  4
• 氢受体数：
  37

反应信息

• 作为反应物：
  描述：

  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→6)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetamide 、 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-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%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)-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-[(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→6))]-3,4-di-O-acetyl-α-D-mannopyranosyl)-(1→6)-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 [(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 在 水 、 溶剂黄146 作用下， 反应 2.0h， 以76%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-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