1-(5-O-benzoyl-2-deoxy-3-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-5-phenyluracil | 259181-66-3

• 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: 1-(5-O-benzoyl-2-deoxy-3-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-5-phenyluracil
• 英文别名: [(2R,3S,5R)-5-(2,4-dioxo-5-phenylpyrimidin-1-yl)-3-methylsulfonyloxyoxolan-2-yl]methyl benzoate
• CAS: 259181-66-3
• 化学式: C₂₃H₂₂N₂O₈S
• 分子量: 486.502
• InChiKey: ZXUNHXAIAAMVLB-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133.76
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-benzoyl-2-deoxy-3-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-5-phenyluracil 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以64%的产率得到2,3'-anhydro-1-(5-O-benzoyl-2-deoxy-3-O-methanesulfonyl-β-D-threo-pentofuranosyl)-5-phenyluracil
  参考文献：
  名称：

  Inhibitory Potency of 5-Benzyluracil, 5-Phenylcytosine and 5-Phenylpyrimidin-2-one Nucleosides Against Uridine Phosphorylase from Mouse Leukemic L1210 Cells

  摘要：

  The inhibitory activity of a series of novel sugar-modified nucleosides derived from 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one against uridine phosphorylase purified from mouse leukemic L-1210 cells was investigated. Significant activity was encountered with O-2,O-2'-anhydro-5-benzylcytidine hydrochloride, 2',3'-dideoxy-5-benzyluridine, 2',3'-dideoxy-4-thiouridine and alpha- and beta-anomers of 5-benzyl-1-(2-deoxy-D-arabino-hexopyranosyl)uracil.

  DOI：

  10.1080/07328319908044626
• 作为产物：
  描述：

  5-苯基-1H-嘧啶-2,4-二酮 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 1-(5-O-benzoyl-2-deoxy-3-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-5-phenyluracil
  参考文献：
  名称：

  Inhibitory Potency of 5-Benzyluracil, 5-Phenylcytosine and 5-Phenylpyrimidin-2-one Nucleosides Against Uridine Phosphorylase from Mouse Leukemic L1210 Cells

  摘要：

  The inhibitory activity of a series of novel sugar-modified nucleosides derived from 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one against uridine phosphorylase purified from mouse leukemic L-1210 cells was investigated. Significant activity was encountered with O-2,O-2'-anhydro-5-benzylcytidine hydrochloride, 2',3'-dideoxy-5-benzyluridine, 2',3'-dideoxy-4-thiouridine and alpha- and beta-anomers of 5-benzyl-1-(2-deoxy-D-arabino-hexopyranosyl)uracil.

  DOI：

  10.1080/07328319908044626