2',3',5'-tris-O-(methoxymethyl)-1-(β-D-arabinofuranosyl)uracil | 149832-01-9

• 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: 2',3',5'-tris-O-(methoxymethyl)-1-(β-D-arabinofuranosyl)uracil
• 英文别名: 1-(2,3,5-tris-O-methoxymethyl-β-D-arabinofuranosyl)uracil
• CAS: 149832-01-9
• 化学式: C₁₅H₂₄N₂O₉
• 分子量: 376.364
• InChiKey: JRISBBKCPLCGIB-RUZUBIRVSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  119.47
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tris-O-(methoxymethyl)-1-(β-D-arabinofuranosyl)uracil 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 反应 36.0h， 生成 1-(β-D-arabinofuranosyl)uracil-6-carboxadehyde
  参考文献：
  名称：

  A new class of nucleosides possessing unusual physical properties: syntheses, hydration, and structural equilibria of 1-(.beta.-D-glycofuranosyl)uracil-6-carboxaldehydes

  摘要：

  The 1-beta-D-ribofruanosyl, 1-(2'-deoxy-beta-D-ribofuranosyl), and 1-beta-D-arabinofuranosyl derivatives (1a-c) of uracil-6-carboxaldehyde have been prepared for physicochemical analysis. The NMR-determined hydration and structural equilibria of 1a-c in both D2O and (CD3)2SO solution are compared, and the single-crystal X-ray structure of 1a is presented. Due to the high degree of electrophilic nature of their aldehyde moiety, all three nucleosides exhibit a strong ProclivitY toward existing as cyclic hemiacetal structures in solution; one such structure was found to be the sole constituent in the solid state for 1a. Using a [formyl-C-13]-labeled derivative of a synthetic precursor to 1a, the 1DELTAC-13(O-18) shielding isotope shift effects produced upon hydrate formation were determined at a +/- 1 ppb level, giving reference values of biomechanistic importance.

  DOI：

  10.1021/jo00067a044
• 作为产物：
  描述：

  二甲醇缩甲醛 、 阿糖尿苷 在 三氟甲磺酸 作用下， 反应 18.0h， 以45%的产率得到2',3',5'-tris-O-(methoxymethyl)-1-(β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Definitive Solution Structures for the 6-Formylated Versions of 1-(βD-Ribofuranosyl)-, 1-(2′-Deoxy-β-D-Ribofuranosyl)-, and 1-β-D-Arabinofuranosyluracil, and of Thymidine

  摘要：

  ROESY and NOESY NMR spectroscopic analyses of the ribofuranosyl (la), 2'-deoxyribofuranosyl (Ib), and arabinofuranosyl (Ic) derivatives of 6-formyluracil in (CD3)(2)SO and D2O solutions have established that each exclusive 7,O5'-cyclic hemiacetal diastereomer of la,b and the major 7,O2'-cyclic hemiacetal diastereomer of Ic possess the 7R configuration. In addition, (7R)-1c has been shown to be thermodynamically more stable than (7S)-1c, contrary to our previous indication. A new, higher yielding synthetic route to in has been developed, Ib has been obtained for the first time in crystalline form, the route to Ic has been modified to better accommodate large scale preparations, and a new, fourth member of this class, 6-formylthymidine (Id), has been synthesized and its solution structures in (CD3)(2)SO, D2O, and CD3OD have been determined. Antitumor and antiviral evaluations of la-e have revealed no significant levels of activity.

  DOI：

  10.1080/07328319608002033