2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-levulinoyl-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose | 247077-89-0

• 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: 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-levulinoyl-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose
• CAS: 247077-89-0
• 化学式: C₅₃H₆₃N₃O₁₅Si
• 分子量: 1010.18
• InChiKey: OILYYTQWGLMDKE-OKCCCBGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  72.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  226.41
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-levulinoyl-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose 在 chromium(VI) oxide 、 4 A molecular sieve 、 硫酸 、 叔丁基二甲硅基三氟甲磺酸酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 12.67h， 生成 methyl [methyl (methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate
  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：

  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 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-levulinoyl-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