(R)-3-Decyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-5H-furan-2-one | 133794-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-Decyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-5H-furan-2-one
• CAS: 133794-60-2
• 化学式: C₂₁H₃₆O₇
• 分子量: 400.513
• InChiKey: BGJFSMPMRKKJLQ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (R)-3-Decyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-5H-furan-2-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以45%的产率得到(2R)-4-decoxy-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-2H-furan-5-one
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.

  DOI：

  10.1021/jm00399a019
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (R)-3-Decyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-5H-furan-2-one
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.

  DOI：

  10.1021/jm00399a019