5-azidopentyl (4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-O-deoxy-β-D-glucopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1363157-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl (4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-O-deoxy-β-D-glucopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 1363157-94-1
• 化学式: C₈₇H₁₀₀N₄O₂₁
• 分子量: 1537.77
• InChiKey: UZDXEGQQYTZVKY-ZIGRAJRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.23
• 重原子数：
  112.0
• 可旋转键数：
  39.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  295.46
• 氢给体数：
  4.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl (4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-O-deoxy-β-D-glucopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 甲酸 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到5-aminopentyl β-D-galactopyranosyl-(1→3)-2-deoxy-2-acetoamido-β-D-galactopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
  参考文献：
  名称：

  Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc₄ and IV²Fuc-Lc₄

  摘要：

  Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.

  DOI：

  10.1021/ja300284x
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 13.0h， 以121.9 mg的产率得到5-azidopentyl (4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-O-deoxy-β-D-glucopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc₄ and IV²Fuc-Lc₄

  摘要：

  Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.

  DOI：

  10.1021/ja300284x