1-(3,5-di-O-(p-toluoyl)-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2,2-difluoroethyl)-4-methoxypyrimidin-2-one | 561320-53-4

• 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-(3,5-di-O-(p-toluoyl)-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2,2-difluoroethyl)-4-methoxypyrimidin-2-one
• 英文别名: [(2R,3S,5R)-5-[5-(2,2-difluoroethyl)-4-methoxy-2-oxopyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 561320-53-4
• 化学式: C₂₈H₂₈F₂N₂O₇
• 分子量: 542.536
• InChiKey: AUGAICMHRBPLHV-WMTXJRDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-O-(p-toluoyl)-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2,2-difluoroethyl)-4-methoxypyrimidin-2-one 在 三甲基氯硅烷 、 sodium iodide 、 sodium hydroxide 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 2.08h， 以87%的产率得到1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-(2,2-difluoroethyl)pyrimidin-2,4(3H)-one
  参考文献：
  名称：

  Synthesis of a Novel Aldehyde: 4-O-Methyl-5-formylmethyl- 2′-deoxyuridine

  摘要：

  The synthesis of the blocked nucleoside 3',5'-di-O-p-toluoyl-4-O-methyl-5-formyl-methyl-2'-deoxyuridine (19) was accomplishied in eleven steps from gamma-butyrolactone. This aldehyde, which should facilitate the synthesis of nucleosides containing F-18, was converted to the corresponding blocked dithianyl nucleoside (21), and also to 5-(2,2-difluoroethyl)-substituted derivatives of 2'-deoxyuridine and 2-deoxycytidine.

  DOI：

  10.1081/ncn-120018624
• 作为产物：
  描述：

  1-(3,5-di-O-(p-toluoyl)-2-deoxy-D-erythro-pentofuranosyl)-5-formylmethyl-4-methoxypyrimidin-2-one 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(3,5-di-O-(p-toluoyl)-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2,2-difluoroethyl)-4-methoxypyrimidin-2-one 、 1-(3,5-di-O-(p-toluoyl)-2-deoxy-α-D-erythro-pentafuranosyl)-5-(2,2-difluoroethyl)-4-methoxypyrimidin-2-one
  参考文献：
  名称：

  Synthesis of a Novel Aldehyde: 4-O-Methyl-5-formylmethyl- 2′-deoxyuridine

  摘要：

  The synthesis of the blocked nucleoside 3',5'-di-O-p-toluoyl-4-O-methyl-5-formyl-methyl-2'-deoxyuridine (19) was accomplishied in eleven steps from gamma-butyrolactone. This aldehyde, which should facilitate the synthesis of nucleosides containing F-18, was converted to the corresponding blocked dithianyl nucleoside (21), and also to 5-(2,2-difluoroethyl)-substituted derivatives of 2'-deoxyuridine and 2-deoxycytidine.

  DOI：

  10.1081/ncn-120018624