methyl uronate | 168432-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl uronate
• CAS: 168432-18-6
• 化学式: C₂₁H₄₄O₇Si₂
• 分子量: 464.747
• InChiKey: QZJSPGPUWVCQDH-HZKQSDJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl uronate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以94%的产率得到methyl 2,3-di-(O-triethylsilyl)-4-O-methyl-α-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis and Rearrangement Reactions of Ester-Linked Lignin-Carbohydrate Model Compounds

  摘要：

  A series of ester-linked lignin-carbohydrate model compounds has been synthesized, which represent possible ester linkages of lignin to hemicellulose in wood through the carboxylic acid group of 4-O-methyl-alpha-D-glucopyranosiduronic acid moieties. The three and erythro isomers of these compounds were prepared through an appropriate combination of protective and stereoselective transformations. Spectroscopic characterization of these esters revealed that the uronosyl group migrated between the primary (gamma) and benzylic (alpha) positions of the lignin side chain in both acidic and neutral conditions. It has been determined that the migration equilibrium favors gamma- over alpha-esters, with the reaction possibly proceeding through a six-membered ring intermediate. That uronosyl migrations occur favoring the gamma-position suggests that the classical view of lignin-xylan ester linkages in wood needs to be reevaluated.

  DOI：

  10.1021/jf00056a026
• 作为产物：
  描述：

  methyl 4-O-methyl-α-D-glucopyranosiduronic acid 在 咪唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl uronate
  参考文献：
  名称：

  Synthesis and Rearrangement Reactions of Ester-Linked Lignin-Carbohydrate Model Compounds

  摘要：

  A series of ester-linked lignin-carbohydrate model compounds has been synthesized, which represent possible ester linkages of lignin to hemicellulose in wood through the carboxylic acid group of 4-O-methyl-alpha-D-glucopyranosiduronic acid moieties. The three and erythro isomers of these compounds were prepared through an appropriate combination of protective and stereoselective transformations. Spectroscopic characterization of these esters revealed that the uronosyl group migrated between the primary (gamma) and benzylic (alpha) positions of the lignin side chain in both acidic and neutral conditions. It has been determined that the migration equilibrium favors gamma- over alpha-esters, with the reaction possibly proceeding through a six-membered ring intermediate. That uronosyl migrations occur favoring the gamma-position suggests that the classical view of lignin-xylan ester linkages in wood needs to be reevaluated.

  DOI：

  10.1021/jf00056a026