1-(α-L-2',3'-dideoxyribofuranosyl)uracil | 158850-65-8

• 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-(α-L-2',3'-dideoxyribofuranosyl)uracil
• 英文别名: 2',3'-dideoxy-α-L-uridine；1-[(2R,5R)-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 158850-65-8
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: BTOTXLJHDSNXMW-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(α-L-2',3'-dideoxyribofuranosyl)uracil 在 potassium phosphate buffer 、 E_. coli purine nucleoside phosphorylase 、 E_. coli thymidine phosphorylase 、 potassium buffer 、 adenosine deaminase 作用下， 反应 24.0h， 生成 9-(α-L-2',3'-dideoxyribofuranosyl)guanine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides

  摘要：

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.

  DOI：

  10.1080/15257779408009473
• 作为产物：
  描述：

  1-(L-2',3'-dideoxyribofuranosyl)cytosine 在 E coli deaminase 作用下， 以 水 为溶剂， 以42%的产率得到1-(α-L-2',3'-dideoxyribofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides

  摘要：

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.

  DOI：

  10.1080/15257779408009473

文献信息

• Expeditious Syntheses of Sugar-Modified Nucleosides and Collections Thereof Exploiting Furan-, Pyrrole-, and Thiophene-Based Siloxy Dienes
  作者：Gloria Rassu、Franca Zanardi、Lucia Battistini、Enrico Gaetani、Giovanni Casiraghi

  DOI：10.1021/jm960400q

  日期：1997.1.1

  enriched 2',3'-dideoxynucleosides 14a-c (alpha and beta anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (alpha and beta anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (beta anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-but

  一系列单独的糖修饰的嘧啶核苷，包括对映体富集的2'，3'-二脱氧核苷14a-c（L和D系列的α和β端基异构体），2'，3'-二脱氧-4'-硫代核苷21a-合成了c（L和D系列的α和β端基异构体）和2'，3'-二脱氧-4'-氮杂核苷28a-c（L和D系列的β端基异构体）立体化学效率，利用三元组的多功能杂环甲硅烷氧基二烯，即2-（叔丁基二甲基甲硅烷氧基）呋喃（TBSOF），2-（叔丁基二甲基甲硅烷氧基）噻吩（TBSOT）和N-（叔丁氧基羰基）-2-（叔丁基二甲基甲硅烷氧基）吡咯（TBSOP）。合成方法有利地使用甘油醛丙酮化物的对映体（D-1和L-1）作为手性来源和甲酰基阳离子的合成等同物。
• Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides
  作者：Naina A. Van Draanen、George W. Koszalka

  DOI：10.1080/15257779408009473

  日期：1994.9

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.