5-azidopentyl (3-O-acetyl-4,6-di-O-benzyl-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 | 1363157-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azidopentyl (3-O-acetyl-4,6-di-O-benzyl-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: 1363157-96-3
• 化学式: C₉₁H₁₀₄N₄O₂₃
• 分子量: 1621.84
• InChiKey: GDDKXKPLGWJCEY-GMMYLHGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.37
• 重原子数：
  118.0
• 可旋转键数：
  41.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  307.6
• 氢给体数：
  2.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl (3-O-acetyl-4,6-di-O-benzyl-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 、 p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到5-azidopentyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-(3-O-acetyl-4,6-di-O-benzyl-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
• 作为产物：
  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 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到5-azidopentyl (3-O-acetyl-4,6-di-O-benzyl-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