β-D-glucopyranuronosylamine sodium salt | 1332462-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranuronosylamine sodium salt
• 英文别名: sodium;(2S,3S,4S,5R,6R)-6-amino-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 1332462-65-3
• 化学式: C₆H₁₀NO₆*Na
• 分子量: 215.138
• InChiKey: NDMLLSVXHGJPMT-VQLXCONVSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -7.49
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  sodium D-glucoronate 在 氨 作用下， 以 水 为溶剂， 反应 48.0h， 以78%的产率得到β-D-glucopyranuronosylamine sodium salt
  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

• NMR and MS study of the formation of β-<scp>d</scp>-glucopyranosylamine uronic acid in aqueous solution
  作者：Ali Ghadban、Luca Albertin、Eric Condamine、Rédéo W. Moussavou Mounguengui、Alain Heyraud

  DOI：10.1139/v11-064

  日期：2011.8

  The products of the reaction of d-glucuronic acid with various combinations of ammonia and volatile ammonium salts in water were studied by NMR and MS spectroscopy. For long reaction times (~24 h), the expected products β-d-glucopyranosylamine uronic acid and ammonium N-(β-d-glucopyranosyluronic acid)carbamate were obtained in good-to-high yield, whereas seven intermediate species were identified in samples taken at earlier reaction times. ¹H–¹H homonuclear and ¹H–¹³C heteronuclear correlation experiments enabled a complete assignment of the ¹H and ¹³C NMR spectra of the starting and final compounds, and a partial assignment of the peaks of intermediate species. Based on these results, a ¹H NMR protocol for the quantification of the different compounds taking part in the reaction was developed, which was used to monitor the evolution of the composition of an early reaction sample redissolved in D₂O. It was thus established that two of the observed intermediate species are actually the α anomer of the main products, whereas the others are precursors to the formation of α/β-d-glucopyranosylamine uronic acid and ammonium N-(α/β-d-glucopyranosyluronic acid)carbamate. The correct assignments for the ¹H and ¹³C spectra of d-glucuronic acid in D₂O are also reported.

  该研究使用核磁共振（NMR）和质谱（MS）光谱研究了d-葡萄糖醛酸与氨和挥发性铵盐在水中反应产物。在长时间反应（约24小时）中，预期产物β-d-葡萄糖吡喃氨基葡糖醛酸和铵盐N-(β-d-葡糖吡喃醛酸)氨基甲酸酯以较高产率得到，而在较早反应时间采集的样品中鉴定了七种中间产物。通过1H-1H同核和1H-13C异核相关实验，完成了起始和最终化合物的1H和13C NMR光谱的完整分配，并对中间产物的峰进行了部分分配。基于这些结果，开发了用于定量参与反应的不同化合物的1H NMR协议，用于监测在D2O中重新溶解的早期反应样品的组成演变。因此确定了观察到的两种中间产物实际上是主要产物的α异构体，而其他产物是α/β-d-葡糖吡喃氨基葡糖醛酸和铵盐N-(α/β-d-葡糖吡喃醛酸)氨基甲酸酯的前体。还报告了在D2O中d-葡糖醛酸的1H和13C光谱的正确分配。