2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose | 247077-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose
• CAS: 247077-88-9
• 化学式: C₄₉H₄₇N₃O₁₃
• 分子量: 885.924
• InChiKey: MVCAGKJUGZWXDX-IEOPPCDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  65.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  192.27
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  A synthetic heparan sulfate pentasaccharide, exclusively containing l -iduronic acid, displays higher affinity for FGF-2 than its d -glucuronic acid-containing isomers

  摘要：

  It has been suggested that the FGF-2 binding site on heparan sulfate chains is a trisulfated pentasaccharide containing three hexuronic acid units. The configuration at C-5 of two of them being undetermined, we have synthesized the four possible pentasaccharides, and have evaluated their FGF-2 binding affinity through in vitro biological assays. The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00106-6
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 、 1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose
  参考文献：
  名称：

  A synthetic heparan sulfate pentasaccharide, exclusively containing l -iduronic acid, displays higher affinity for FGF-2 than its d -glucuronic acid-containing isomers

  摘要：

  It has been suggested that the FGF-2 binding site on heparan sulfate chains is a trisulfated pentasaccharide containing three hexuronic acid units. The configuration at C-5 of two of them being undetermined, we have synthesized the four possible pentasaccharides, and have evaluated their FGF-2 binding affinity through in vitro biological assays. The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00106-6