4-methoxyphenyl O-(benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronate | 1616628-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl O-(benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronate
• CAS: 1616628-10-4
• 化学式: C₇₈H₇₄Cl₃NO₂₂
• 分子量: 1483.8
• InChiKey: IXCZLQKAUVCRGH-AHKQPLAASA-N

物化性质

• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.49
• 重原子数：
  104.0
• 可旋转键数：
  29.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  273.13
• 氢给体数：
  2.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  O-(4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α,β-D-glucopyranosyl)trichloroacetimidate 、 4-methoxyphenyl O-(benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以64%的产率得到4-methoxyphenyl O-(4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-O-(benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate
  参考文献：
  名称：

  Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

  摘要：

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.007
• 作为产物：
  描述：

  4-methoxyphenyl O-(benzyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronate 在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到4-methoxyphenyl O-(benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-(1→3)-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1→4)-benzyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronate
  参考文献：
  名称：

  Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

  摘要：

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.007