phenyl {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-1-thio-α-D-mannopyranoside | 1492048-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl {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-1-thio-α-D-mannopyranoside
• CAS: 1492048-30-2
• 化学式: C₄₆H₅₆Cl₆N₂O₂₅S
• 分子量: 1281.73
• InChiKey: GHWGCAOVEQIGTF-ONFKGPFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  80.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  333.21
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  phenyl {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-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 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→6)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetamide
  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 {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-O-(2',3'-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside 、 乙酸酐 在 三氟乙酸 、 吡啶 作用下， 以 水 为溶剂， 反应 15.17h， 以82%的产率得到phenyl {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-1-thio-α-D-mannopyranoside
  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