N-(benzyl)-benzyloxycarbonyl-5-aminopentyl 2-azido-3-O-benzyl-2-deoxy-6-O-tert-butyl-diphenylsilyl-α-D-glucopyranoside | 1610447-40-9

• 分子结构分类: 有机化合物
• 英文名称: N-(benzyl)-benzyloxycarbonyl-5-aminopentyl 2-azido-3-O-benzyl-2-deoxy-6-O-tert-butyl-diphenylsilyl-α-D-glucopyranoside
• CAS: 1610447-40-9
• 化学式: C₄₉H₅₈N₄O₇Si
• 分子量: 843.108
• InChiKey: FCOQGJJPERRCOF-JHPAFTAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  61.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  135.45
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(benzyl)-benzyloxycarbonyl-5-aminopentyl 2-azido-3-O-benzyl-2-deoxy-6-O-tert-butyl-diphenylsilyl-α-D-glucopyranoside 在 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N-(benzyl)-benzyloxycarbonyl-5-aminopentyl O-(3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1→4)-O-2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Unique Heparin Mimetic Hexasaccharide for Structure–Activity Relationship Studies

  摘要：

  To date, the structure-activity relationship studies of heparin/heparan sulfate with their diverse binding partners such as growth factors, cytokines, chemokines, and extracellular matrix proteins have been limited yet provide early insight that specific sequences contribute to this manifold biological role. This has led to an impetus for the chemical synthesis of oligosaccharide fragments of these complex polysaccharides, which can provide an effective tool for this goal. The synthesis of three heparin mimetic hexasaccharides with distinct structural patterns is described herein, and the influence of the targeted substitution on their bioactivity profiles is studied using in vitro affinity and/or inhibition toward different growth factors and proteins. Additionally, the particularly challenging synthesis of an irregular hexasaccharide is reported, which, interestingly, in spite of being considerably structurally similar with its two counterparts, displayed a unique and remarkably distinct profile in the test assays.

  DOI：

  10.1021/jm4016069
• 作为产物：
  描述：

  N-(benzyl)-benzyloxycarbonyl-5-aminopentyl O-2-azido-3-O-benzyl-2-deoxy-α-D-glycopyranoside 、 叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到N-(benzyl)-benzyloxycarbonyl-5-aminopentyl 2-azido-3-O-benzyl-2-deoxy-6-O-tert-butyl-diphenylsilyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Unique Heparin Mimetic Hexasaccharide for Structure–Activity Relationship Studies

  摘要：

  To date, the structure-activity relationship studies of heparin/heparan sulfate with their diverse binding partners such as growth factors, cytokines, chemokines, and extracellular matrix proteins have been limited yet provide early insight that specific sequences contribute to this manifold biological role. This has led to an impetus for the chemical synthesis of oligosaccharide fragments of these complex polysaccharides, which can provide an effective tool for this goal. The synthesis of three heparin mimetic hexasaccharides with distinct structural patterns is described herein, and the influence of the targeted substitution on their bioactivity profiles is studied using in vitro affinity and/or inhibition toward different growth factors and proteins. Additionally, the particularly challenging synthesis of an irregular hexasaccharide is reported, which, interestingly, in spite of being considerably structurally similar with its two counterparts, displayed a unique and remarkably distinct profile in the test assays.

  DOI：

  10.1021/jm4016069