sodium;N-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-2-methylprop-2-enimidate | 1344124-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium;N-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-2-methylprop-2-enimidate
• CAS: 1344124-99-7
• 化学式: C₁₀H₁₄NO₇*Na
• 分子量: 283.213
• InChiKey: BLUXTACKWKXLDX-IGJMQZEWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.78
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲基丙烯酸酐 、 sodium D-glucoronate 在 氨基甲酸铵 、 sodium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 49.0h， 生成 sodium;N-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-2-methylprop-2-enimidate
  参考文献：
  名称：

  Synthesis of β-d-glucopyranuronosylamine in aqueous solution: kinetic study and synthetic potential

  摘要：

  A systematic study of the synthesis of beta-D-glucopyranuronosylamine in water is reported. When sodium D-glucuronate was reacted with ammonia and/or volatile ammonium salts in water a mixture of beta-D-glucopyranuronosylamine and ammonium N-8-D-glucopyranuronosyl carbamate was obtained at a rate that strongly depended on the experimental conditions. In general higher ammonia and/or ammonium salt concentrations led to a faster conversion of the starting sugar into intermediate species and of the latter into the final products. Yet, some interesting trends and exceptions were observed. The use of saturated ammonium carbamate led to the fastest rates and the highest final yields of beta-D-glucopyranuronosylamine/carbamate. With the exception of 1 M ammonia and 0.6 M ammonium salt, after 24 h of reaction all tested protocols led to higher yields of beta-glycosylamine/carbamate than concentrated commercial ammonia alone. The mole fraction of alpha-D-glucopyranuronosylamine/carbamate at equilibrium was found to be 7-8% in water at 30 degrees C. Concerning bis(beta-D-glucopyranuronosyl)amine, less than 3% of it is formed in all cases, with a minimum value of 0.5% in the case of saturated ammonium carbamate. Surprisingly, the reaction was consistently faster in the case of sodium D-glucuronate than in the case of D-glucose (4-8 times faster). Finally, the synthetic usefulness of our approach was demonstrated by the synthesis of three N-acyl-beta-D-glucopyranuronosylamines and one N-alkylcarbamoyl-beta-D-glucopyranuronosylamine directly in aqueous-organic solution without resorting to protective group chemistry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.018

文献信息

• Synthesis of β-d-glucopyranuronosylamine in aqueous solution: kinetic study and synthetic potential
  作者：Ali Ghadban、Luca Albertin、Rédéo W. Moussavou Mounguengui、Alexandre Peruchon、Alain Heyraud

  DOI：10.1016/j.carres.2011.08.018

  日期：2011.11

  A systematic study of the synthesis of beta-D-glucopyranuronosylamine in water is reported. When sodium D-glucuronate was reacted with ammonia and/or volatile ammonium salts in water a mixture of beta-D-glucopyranuronosylamine and ammonium N-8-D-glucopyranuronosyl carbamate was obtained at a rate that strongly depended on the experimental conditions. In general higher ammonia and/or ammonium salt concentrations led to a faster conversion of the starting sugar into intermediate species and of the latter into the final products. Yet, some interesting trends and exceptions were observed. The use of saturated ammonium carbamate led to the fastest rates and the highest final yields of beta-D-glucopyranuronosylamine/carbamate. With the exception of 1 M ammonia and 0.6 M ammonium salt, after 24 h of reaction all tested protocols led to higher yields of beta-glycosylamine/carbamate than concentrated commercial ammonia alone. The mole fraction of alpha-D-glucopyranuronosylamine/carbamate at equilibrium was found to be 7-8% in water at 30 degrees C. Concerning bis(beta-D-glucopyranuronosyl)amine, less than 3% of it is formed in all cases, with a minimum value of 0.5% in the case of saturated ammonium carbamate. Surprisingly, the reaction was consistently faster in the case of sodium D-glucuronate than in the case of D-glucose (4-8 times faster). Finally, the synthetic usefulness of our approach was demonstrated by the synthesis of three N-acyl-beta-D-glucopyranuronosylamines and one N-alkylcarbamoyl-beta-D-glucopyranuronosylamine directly in aqueous-organic solution without resorting to protective group chemistry. (C) 2011 Elsevier Ltd. All rights reserved.