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 | 1616628-07-9

• 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-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
• 英文别名: N-[(2S,3R,4R,5S,6R)-5-acetyloxy-2-[(2S,3S,4S,5R,6S)-5-benzoyloxy-6-(4-methoxyphenoxy)-4-phenylmethoxy-2-phenylmethoxycarbonyloxan-3-yl]oxy-4-[(2R,3R,4S,5S,6S)-3-benzoyloxy-5-(4-oxopentanoyloxy)-4-phenylmethoxy-6-phenylmethoxycarbonyloxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-3-yl]-2,2,2-trichloroethanimidic acid
• CAS: 1616628-07-9
• 化学式: C₈₃H₈₀Cl₃NO₂₄
• 分子量: 1581.9
• InChiKey: JFFZKKLUQYDNNZ-YQXHXQDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  111
• 可旋转键数：
  39
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  300
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  O-(benzyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate) trichloroacetimidate 、 benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以41%的产率得到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
  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