(R)-4-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)butane-1,3-diol | 1491018-02-0

• 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: (R)-4-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)butane-1,3-diol
• CAS: 1491018-02-0
• 化学式: C₂₄H₃₂O₆
• 分子量: 416.514
• InChiKey: IHMUPAYDZJWXQD-ONTLXTELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)butane-1,3-diol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 以43%的产率得到(R)-4-((2S,4R,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)-butane-1,3-diol
  参考文献：
  名称：

  Hydrogen-Bond Networks: Strengths of Different Types of Hydrogen Bonds and An Alternative to the Low Barrier Hydrogen-Bond Proposal

  摘要：

  We report quantifying the strengths of different types of hydrogen bonds in hydrogen-bond networks (HBNs) via measurement of the adiabatic electron detachment energy of the conjugate base of a small covalent polyol model compound (i.e., (HOCH2CH2CH(OH)CH2)(2)CHOH) in the gas phase and the pK(a) of the corresponding acid in DMSO. The latter result reveals that the hydrogen bonds to the charged center and those that are one solvation shell further away (i.e., primary and secondary) provide 5.3 and 2.5 pK(a) units of stabilization per hydrogen bond in DMSO. Computations indicate that these energies increase to 8.4 and 3.9 pK(a) units in benzene and that the total stabilizations are 16 (DMSO) and 25 (benzene) pK(a) units. Calculations on a larger linear heptaol (i.e., (HOCH2CH2CH(OH)CH2CH(OH)CH2)(2)CHOH) reveal that the terminal hydroxyl groups each contribute 0.6 pK(a) units of stabilization in DMSO and 1.1 pK(a) units in benzene. All of these results taken together indicate that the presence of a charged center can provide a powerful energetic driving force for enzyme catalysis and conformational changes such as in protein folding due to multiple hydrogen bonds in a HBN.

  DOI：

  10.1021/ja408762r
• 作为产物：
  描述：

  (R)-1-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol 在 四氧化锇 、 N-甲基吗啉氧化物 、 sodium periodate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.08h， 以69%的产率得到(R)-4-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)butane-1,3-diol
  参考文献：
  名称：

  Hydrogen-Bond Networks: Strengths of Different Types of Hydrogen Bonds and An Alternative to the Low Barrier Hydrogen-Bond Proposal

  摘要：

  We report quantifying the strengths of different types of hydrogen bonds in hydrogen-bond networks (HBNs) via measurement of the adiabatic electron detachment energy of the conjugate base of a small covalent polyol model compound (i.e., (HOCH2CH2CH(OH)CH2)(2)CHOH) in the gas phase and the pK(a) of the corresponding acid in DMSO. The latter result reveals that the hydrogen bonds to the charged center and those that are one solvation shell further away (i.e., primary and secondary) provide 5.3 and 2.5 pK(a) units of stabilization per hydrogen bond in DMSO. Computations indicate that these energies increase to 8.4 and 3.9 pK(a) units in benzene and that the total stabilizations are 16 (DMSO) and 25 (benzene) pK(a) units. Calculations on a larger linear heptaol (i.e., (HOCH2CH2CH(OH)CH2CH(OH)CH2)(2)CHOH) reveal that the terminal hydroxyl groups each contribute 0.6 pK(a) units of stabilization in DMSO and 1.1 pK(a) units in benzene. All of these results taken together indicate that the presence of a charged center can provide a powerful energetic driving force for enzyme catalysis and conformational changes such as in protein folding due to multiple hydrogen bonds in a HBN.

  DOI：

  10.1021/ja408762r