1-(5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)uracil | 612485-29-7

• 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-(5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)uracil
• CAS: 612485-29-7
• 化学式: C₁₇H₁₅N₃O₆
• 分子量: 357.323
• InChiKey: JOWACRSMSMEIHJ-JURCDPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134.67
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)uracil 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以83%的产率得到1-(3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and anti-HIV activity of l-β-3′-C-cyano-2′,3′-unsaturated nucleosides and l-3′-C-cyano-3′-deoxyribonucleosides

  摘要：

  An efficient synthetic method was developed for L-beta-3'-C-cyano-2',3'-unsaturated nucleosides and L-3'-C-cyano-3'-deoxyribonucleosides. The key intermediate 11 was obtained from L-xylose, from which a series of pyrimidine and purine nucleosides were prepared in high yield by the coupling of 11 and various silyl-protected bases in the presence of TMSOTf. These nucleosides were eliminated, followed by deprotecting to give L-beta-3'-C-cyano-2',3'-unsaturated nucleosides. When selectively deprotected by hydrazine hydrate in buffered acetic acid-pyridine followed by treatment with potassium carbonate in methanol, L-3'-C-cyano-3'-deoxyribonucleosides were obtained. The synthesized nucleosides were tested for anti-HIV activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01074-3
• 作为产物：
  描述：

  3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-L-ribofuranose 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 一水合肼 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 57.0h， 生成 1-(5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and anti-HIV activity of l-β-3′-C-cyano-2′,3′-unsaturated nucleosides and l-3′-C-cyano-3′-deoxyribonucleosides

  摘要：

  An efficient synthetic method was developed for L-beta-3'-C-cyano-2',3'-unsaturated nucleosides and L-3'-C-cyano-3'-deoxyribonucleosides. The key intermediate 11 was obtained from L-xylose, from which a series of pyrimidine and purine nucleosides were prepared in high yield by the coupling of 11 and various silyl-protected bases in the presence of TMSOTf. These nucleosides were eliminated, followed by deprotecting to give L-beta-3'-C-cyano-2',3'-unsaturated nucleosides. When selectively deprotected by hydrazine hydrate in buffered acetic acid-pyridine followed by treatment with potassium carbonate in methanol, L-3'-C-cyano-3'-deoxyribonucleosides were obtained. The synthesized nucleosides were tested for anti-HIV activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01074-3