1-(5-azido-5-deoxy-2,3-epoxy-β-D-lyxofuranosyl)uracil | 141917-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(5-azido-5-deoxy-2,3-epoxy-β-D-lyxofuranosyl)uracil
• 英文别名: 1-[(1S,2R,4R,5S)-4-(azidomethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]pyrimidine-2,4-dione
• CAS: 141917-16-0
• 化学式: C₉H₉N₅O₄
• 分子量: 251.202
• InChiKey: SOIYJCSPVUMDAW-YDKYIBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-azido-5-deoxy-2,3-epoxy-β-D-lyxofuranosyl)uracil 在 钯 吡啶 、 sodium azide 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~100.0 ℃ 、350.0 kPa 条件下， 反应 66.75h， 生成 1-(2-O-acetyl-3-azido-5-benzamido-3,5-dideoxy-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
• 作为产物：
  描述：

  2',3',5'-tri-O-methylsulfonyluridine 在 sodium hydroxide 、 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-(5-azido-5-deoxy-2,3-epoxy-β-D-lyxofuranosyl)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

文献信息

• An Efficient Route to Pyrimidine Nucleosides with the 2,3-Anhydro-β-<scp>d</scp>-lyxofuranosyl Stereochemistry
  作者：Todd Lowary、Christopher Callam、Rajendrakumar Gadikota

  DOI：10.1055/s-2003-40335

  日期：——

  Described is the efficient preparation of 2,3-anhydro-β-d-lyxofuranosyl pyrimidine nucleosides via the coupling of a 2,3-anhydrosugar-containing glycosyl donor (5 or 6) with a silylated nucleoside base. The products are obtained with a high degree of stereoselectivity and in 65-77% yield.

  描述了通过将含有2,3-脱水糖的糖基供体（5或6）与硅烷化核苷碱基偶联，高效制备2,3-脱水-β-d-来苏糖呋喃核苷的过程。所得产物具有高度的立体选择性，收率为65-77%。