(3S,4S,5S,6S)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one | 110115-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5S,6S)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
• 英文别名: L-Gulono-1,5-lactone；(3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• CAS: 110115-45-2
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: PHOQVHQSTUBQQK-QTBDOELSSA-N

物化性质

• 沸点：
  446.4±38.0 °C(Predicted)
• 密度：
  1.720±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-古洛糖酸 以 重水 为溶剂， 生成 (3S,4S,5S,6S)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  L-古洛糖酸的酸度和自催化内酯化作用：热力学，动力学和计算研究

  摘要：

  糖酸的酸化和质子解离在酸性水溶液中同时发生。质子-去质子化过程总是很快，而γ-和δ-内酯的形成和水解通常较慢。因此，完整理解这些反应需要热力学和动力学信息。从电位和极化测量结果确定了古龙酸酯（Gul-）的质子化常数（Kp），而通过13 C NMR实验获得了1-古洛糖酸（HGul）的各个内酯化常数（KL，γ和KL，δ）。通过测量d-葡萄糖酸（HGluc）的这些众所周知的常数并将其与文献数据进行比较，证明了该方法的适用性。l-古洛糖酸γ-内酯（γ-HGul）与δ-HGul以及γ-和δ-HGluc相比具有显着的稳定性。极化测量表明，负责提高γ-HGul稳定性的主要因素是其水解比δ-HGul的水解慢得多。γ-HGul环相对于其δ-异构体的更高稳定性也通过量子化学计算得到了证实。该反应的一个新证实的特征是，与其他H3O +平行，HGul还催化γ-HGul的形成和逆水解过程，这与其他普通酸催化剂相似。

  DOI：

  10.1016/j.carres.2018.07.006

文献信息

• COMPOSITIONS AND METHODS FOR ENHANCING PLANT GROWTH
  申请人：NOVOZYMES BIOAG A/S

  公开号：US20140087944A1

  公开（公告）日：2014-03-27

  Described herein are compositions comprising one or more gluconolactones for enhancing plant growth and methods for treating plants, plant parts, or soils with one or more gluconolactones for enhancing plant growth.
• 10.1002/cctc.202400411
  作者：Bandyopadhyay, Uchchhal、Lancien, Antoine、Branquet, David、Lhoste, Jérôme、Comesse, Sébastien、Martel, Arnaud、Benhamou, Laure

  DOI：10.1002/cctc.202400411

  日期：——

  Knölker complexes have been recently used to perform the catalytic C1‐oxidation of unprotected sugars into sugar lactones. This oxidation method remained limited by the stability of the catalyst with the polyhydroxylated substrates. Our objective is now to overcome these limitations and extend this method to more challenging substrates such as disaccharides. We proposed in this paper two original designs of Knölker‐type complexes conceived to promote secondary H‐bond interactions with the OH groups of the substrates to stabilise the system and favour the transformation. In total, 8 novel pre‐catalysts were synthesised, fully characterised and applied in the anomeric oxidation of several sugar derivatives. Two of these new complexes proved to be more efficient than the Knölker complex for the oxidation of disaccharides. Moreover, a preliminary DFT study revealed the presence of H‐bonds interactions between the substrate and the oxygen atom on the ligand arm of the best complexes suggesting a beneficial role of this heteroatom on the catalytic efficiency.
• The acidity and self-catalyzed lactonization of l-gulonic acid: Thermodynamic, kinetic and computational study
  作者：Bence Kutus、Gábor Peintler、Ákos Buckó、Zsolt Balla、Alexandru Lupan、Amr A.A. Attia、István Pálinkó、Pál Sipos

  DOI：10.1016/j.carres.2018.07.006

  日期：2018.9

  polarimetric measurements, while the individual lactonization constants (KL,γ and KL,δ) for l-gulonic acid (HGul) were obtained via13C NMR experiments. The applicability of this method was proven by measuring these well-known constants for d-gluconic acid (HGluc) and by comparing them to literature data. l-gulonic acid γ-lactone (γ-HGul) has remarkable stability in contrast with δ-HGul as well as γ- and δ-HGluc

  糖酸的酸化和质子解离在酸性水溶液中同时发生。质子-去质子化过程总是很快，而γ-和δ-内酯的形成和水解通常较慢。因此，完整理解这些反应需要热力学和动力学信息。从电位和极化测量结果确定了古龙酸酯（Gul-）的质子化常数（Kp），而通过13 C NMR实验获得了1-古洛糖酸（HGul）的各个内酯化常数（KL，γ和KL，δ）。通过测量d-葡萄糖酸（HGluc）的这些众所周知的常数并将其与文献数据进行比较，证明了该方法的适用性。l-古洛糖酸γ-内酯（γ-HGul）与δ-HGul以及γ-和δ-HGluc相比具有显着的稳定性。极化测量表明，负责提高γ-HGul稳定性的主要因素是其水解比δ-HGul的水解慢得多。γ-HGul环相对于其δ-异构体的更高稳定性也通过量子化学计算得到了证实。该反应的一个新证实的特征是，与其他H3O +平行，HGul还催化γ-HGul的形成和逆水解过程，这与其他普通酸催化剂相似。