1-(5-azido-5-deoxy-β-D-lyxofuranosyl)uracil | 156357-70-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-(5-azido-5-deoxy-β-D-lyxofuranosyl)uracil
• 英文别名: 1-(5-azido-5-deoxy-β-lyxofuranosyl)uracil；1-[(2R,3S,4R,5R)-5-(azidomethyl)-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 156357-70-9
• 化学式: C₉H₁₁N₅O₅
• 分子量: 269.217
• InChiKey: ZXEWVLLJHQSJOW-YDKYIBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  153.31
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(5-azido-5-deoxy-β-D-lyxofuranosyl)uracil 、 丙酮 在 硫酸 、 copper(II) sulfate 作用下， 反应 45.0h， 以92.5%的产率得到1-(5-azido-5-deoxy-2,3-O-isopropylidene-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
• 作为产物：
  描述：

  2,2'-anhydro-1-(5-azido-5-deoxy-3-O-methylsulfonyl-β-D-arabinofuranosyl)uracil 在 水 作用下， 反应 3.0h， 以94%的产率得到1-(5-azido-5-deoxy-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

• A novel type of nucleoside analogue with penta-coordinated phosphorus
  作者：Darinka Katalenić、Vinko Škarić、Branimir Klaić

  DOI：10.1016/s0040-4039(00)77021-3

  日期：1994.4

  The reaction of 1-(5-azido-5-deoxy-β-d-lyxofuranosyl)uracil (3) with triphenyl phosphite afforded a cyclic phosphorane (6) rather than the anticipated 5′-phosphoramido lyxoside (4). The structure of this nucleoside analogue with penta-coordinated phosphorus is based on 1H, 13C and 31P NMR spectra.

  1-（5-叠氮基5-脱氧-β-d-呋喃呋喃糖基）尿嘧啶（3）与亚磷酸三苯酯的反应提供了环磷烷（6），而不是预期的5'-磷酰胺基lyxoside（4）。具有五配位磷的该核苷类似物的结构基于1 H，13 C和31 P NMR光谱。