9-(3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)guanosine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)guanosine
• 英文别名: (2R,5S)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)-2,5-dihydrofuran-3-carbonitrile
• 化学式: C₁₁H₁₀N₆O₃
• 分子量: 274.239
• InChiKey: LMGBMSXOHPVTDA-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N²-acetyl-6-O-diphenylcarbamoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)guanine 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 一水合肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.33h， 生成 9-(3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)guanosine
  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.