9-(3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine
• 英文别名: (2R,3R,4S,5S)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-carbonitrile；(2R,3R,4S,5S)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolane-3-carbonitrile
• 化学式: C₁₁H₁₂N₆O₃
• 分子量: 276.255
• InChiKey: PGZCHDSYRDIAPC-WCGHZBPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,2-di-O-acetyl-5-O-benzoyl-3-C-cyano-3-deoxy-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 、 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 50.33h， 生成 9-(3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine
  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

文献信息

• Synthesis and anti-HIV activity of l-β-3′-C-cyano-2′,3′-unsaturated nucleosides and l-3′-C-cyano-3′-deoxyribonucleosides
  作者：Wei Zhu、Giuseppe Gumina、Raymond F Schinazi、Chung K Chu

  DOI：10.1016/s0040-4020(03)01074-3

  日期：2003.8

  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.