Benzoic acid (2R,3S,5R)-3-hydroxy-5-((5R,6S)-6-hydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 373391-49-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Benzoic acid (2R,3S,5R)-3-hydroxy-5-((5R,6S)-6-hydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS: 373391-49-2
• 化学式: C₁₇H₂₀N₂O₇
• 分子量: 364.355
• InChiKey: NANZEYAZOTUHER-GWJZTGGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  125.4
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S,5R)-3-hydroxy-5-((5R,6S)-6-hydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 以 phosphate buffer 、 乙腈 为溶剂， 生成 5'-benzoylthymidine
  参考文献：
  名称：

  Direct measurement of pyrimidine C6-hydrate stability

  摘要：

  Pyrimidine C6-hydrates are produced via UV-irradiation and undergo dehydration upon standing. The stability of these compounds has a direct bearing on their genotoxicity. The rate constants for elimination from 5 ' -benzyoylated derivatives of 5,6-dihydro-5-hydroxythymidine (6) and 5,6-dihydro-5-hydroxy-2 ' -deoxyuridine (9) were measured directly via HPLC. The rate constants for dehydration increase from pH 6.0 to 8.0. The half-lives for 6 and 9 at pH 7.4 and 37 degreesC are 46.5 and 24.4 h, respectively. Deglycosylation is not observed, even upon heating at 90 degreesC. These observations reinforce proposals that pyrimidine hydrates are sufficiently long-lived that they can exert significant effects on biological systems. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00137-7
• 作为产物：
  描述：

  在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以28%的产率得到Benzoic acid (2R,3S,5R)-3-hydroxy-5-((5R,6S)-6-hydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Direct measurement of pyrimidine C6-hydrate stability

  摘要：

  Pyrimidine C6-hydrates are produced via UV-irradiation and undergo dehydration upon standing. The stability of these compounds has a direct bearing on their genotoxicity. The rate constants for elimination from 5 ' -benzyoylated derivatives of 5,6-dihydro-5-hydroxythymidine (6) and 5,6-dihydro-5-hydroxy-2 ' -deoxyuridine (9) were measured directly via HPLC. The rate constants for dehydration increase from pH 6.0 to 8.0. The half-lives for 6 and 9 at pH 7.4 and 37 degreesC are 46.5 and 24.4 h, respectively. Deglycosylation is not observed, even upon heating at 90 degreesC. These observations reinforce proposals that pyrimidine hydrates are sufficiently long-lived that they can exert significant effects on biological systems. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00137-7