5-azidopentyl (2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1363157-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl (2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 1363157-93-0
• 化学式: C₁₀₂H₁₂₀N₄O₂₃Si
• 分子量: 1798.17
• InChiKey: HOLVTLVGDKEQNC-NHAZNTHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  130.0
• 可旋转键数：
  44.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  296.6
• 氢给体数：
  1.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl (2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成
  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：

  、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 18.0h， 以186.5 mg的产率得到5-azidopentyl (2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-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