methyl O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-2-N-acetyl-2-deoxy-β-D-glucopyranoside | 1191081-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-2-N-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)b-GlcNAc1Me；(2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1191081-84-1
• 化学式: C₇₁H₁₀₉N₅O₅₆
• 分子量: 1928.65
• InChiKey: HZKMRQPBRALVNN-HMVUWWIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -17.4
• 重原子数：
  132
• 可旋转键数：
  34
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  941
• 氢给体数：
  31
• 氢受体数：
  56

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-6-[(2S,3S,4R,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-6-[(2S,3S,4R,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-6-[(2S,3S,4R,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-6-[(2S,3S,4R,5R,6R)-6-[[(2R,4aR,6R,7R,8R,8aS)-7-acetamido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-2-carboxy-5-hydroxy-4-phenylmethoxyoxan-3-yl]oxy-7-acetamido-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-2-carboxy-5-hydroxy-4-phenylmethoxyoxan-3-yl]oxy-7-acetamido-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-2-carboxy-5-hydroxy-4-phenylmethoxyoxan-3-yl]oxy-7-acetamido-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-2-carboxy-5-hydroxy-4-phenylmethoxyoxan-3-yl]oxy-7-acetamido-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,5-dihydroxy-4-phenylmethoxyoxane-2-carboxylic acid 在 氢气 、 palladium(II) hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 72.0h， 以6.6 mg的产率得到methyl O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-O-(2-N-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(β-D-glucopyranosyluronic acid)-(1->3)-2-N-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  一种透明质酸十糖的化学合成

  摘要：

  描述了使用基于预活化的化学选择性糖基化策略的透明质酸十糖的化学合成。由于糖基化和去保护的难度增加，大寡糖的组装通常具有挑战性。事实上，以前用于透明质酸六糖合成的相同结构单元未能产生所需的十糖。经过大量实验，成功构建了十糖主链，二糖构建块的总产率为 37%。三氯乙酰基用作葡糖胺单元的氮保护基团，发现添加 TMSOTf 对抑制三氯甲基恶唑啉副产物的形成和实现高糖基化产率至关重要。对于脱保护，1 H NMR 可以去除所有碱不稳定的保护基团，这有助于生成完全脱保护的 HA 十糖。

  DOI：

  10.1021/jo9016925