methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-β-D-glucopyranose | 247077-97-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-β-D-glucopyranose
• CAS: 247077-97-0
• 化学式: C₃₀H₃₇N₃O₁₆
• 分子量: 695.634
• InChiKey: GCMGYZZPABUREQ-STEZGOMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  243.48
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-β-D-glucopyranose 在 苄胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-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
• 作为产物：
  描述：

  1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 、 methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-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