1-(2-O-acetyl-5-benzamido-3,5-dideoxy-3-diphenylphosphoramido-β-D-arabinofuranosyl)uracil | 141917-41-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-(2-O-acetyl-5-benzamido-3,5-dideoxy-3-diphenylphosphoramido-β-D-arabinofuranosyl)uracil
• CAS: 141917-41-1
• 化学式: C₃₀H₂₉N₄O₉P
• 分子量: 620.555
• InChiKey: VXSZVCAISBRKOL-SKQKNPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  167.05
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2',3',5'-tri-O-methylsulfonyluridine 在 钯 吡啶 、 sodium hydroxide 、 sodium azide 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~100.0 ℃ 、350.0 kPa 条件下， 反应 76.5h， 生成 1-(2-O-acetyl-5-benzamido-3,5-dideoxy-3-diphenylphosphoramido-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Azido-(amino-)furanosyl nucleosides and their phosphoramidates

  摘要：

  The ring-opening of 2,2'-anhydro-1-[5-azido- 5 and 5-benzamido- 3 5-deoxy-3-O-methylsulfonyl-beta-D-arabinofuranosyl] uracil by the ion exchanger Dowex 50 (H+) afforded the corresponding 1-[5-azido-8 and 5-benzamido- 12 5-deoxy-3-O-methylsulfonyl-beta-D-arabinofuranosyl]uracil. Hydrogenolysis of the azido nucleosides over Pd-black in the presence of benzoic acid anhydride led to the corresponding benzamido nucleosides in high yields. The 5'-azido-2',3'-oxirane 10 on reaction with ethanolic ammonia generated 1-(3-amino-5-azido-3,5-dideoxy-beta-D-arabinofuranosyl)uracil 15 and 1-(2-amino-5-azido-2,5-dideoxy-beta-D-xylofuranosyl)uracil 16 in a ratio 2:1. The 5'-O-mesyl-2',3'-oxirane 25, on being treated with NaN3 in DMF at 100-degrees-C, afforded 2',5'-anhydro-1-(3-azido-3-deoxy-beta-D-arabinofuranosyl) uracil 26 (54.5%), 3',5'-diazido-beta-D-arabinofuranosyl 27 (20.6%) and 2',5'-diazido-beta-D-xylofuranosyl 28 (5.4%). The hydrogenolysis of 5 over Pd-black proceeded into 2,5'-imino-1-(3-O-methylsulfonyl-beta-D-arabinofuranosyl)uracil 32 which, as the 5'-benzamido derivative 36, was transformed into 3. The 5'-azido compound 5 and 10 on reaction with triphenyl phosphite in aqueous dioxane gave the respective 5'-diphenylphosphoramidate 38 and 39. Similarly, the 3'-azido compound 22 was converted into 3'-diphenylphosphoramidate 40.

  DOI：

  10.1039/p19920001065