methyl uronate | 130278-32-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl uronate
• 英文别名: methyl [methyl 4-O-(2-azido-6-O-benzoyl-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosid]uronate；methyl (2S,3S,4S,5R,6R)-3-[(2S,3R,4R,5R,6R)-3-azido-6-(benzoyloxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-6-methoxy-4,5-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 130278-32-9
• 化学式: C₄₉H₅₁N₃O₁₂
• 分子量: 873.957
• InChiKey: OJONDGQCSQNCPY-KPOQREGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  175.2
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl uronate 在 sodium hydroxide 、 三甲基铵三氧化硫共聚物 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 28.0h， 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
• 作为产物：
  描述：

  2-azido-6-O-benzoyl-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl trichloroacetimidate 在 重铬酸吡啶 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 methyl uronate
  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

文献信息

• JACQUINET, JEAN-CLAUDE, CARBOHYDR. RES., 199,(1990) N, C. 153-181
  作者：JACQUINET, JEAN-CLAUDE

  DOI：——

  日期：——