methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt | 130278-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt
• CAS: 130278-33-0
• 化学式: C₄₃H₄₇NO₁₅S*2Na
• 分子量: 895.889
• InChiKey: RVSVBMJWYIWOPG-JHOIVDPBSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  61.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  209.5
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以89%的产率得到sodium ((2R,3S,4R,5R,6R)-5-acetamido-6-(((2S,3S,4R,5R,6S)-2-carboxy-4,5-dihydroxy-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)methyl sulfate
  参考文献：
  名称：

  Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate

  摘要：

  3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosiduronic acid and the 6-O-sulfo analogue.

  DOI：

  10.1016/0008-6215(90)84259-w
• 作为产物：
  描述：

  methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid 在 sodium hydroxide 、 三甲基铵三氧化硫共聚物 作用下， 生成 methyl 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt
  参考文献：
  名称：

  Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate

  摘要：

  3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosiduronic acid and the 6-O-sulfo analogue.

  DOI：

  10.1016/0008-6215(90)84259-w