N²-acetyl-6-O-diphenylcarbamoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)guanosine | 612485-33-3

• 分子结构分类: 有机化合物
• 英文名称: N²-acetyl-6-O-diphenylcarbamoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)guanosine
• CAS: 612485-33-3
• 化学式: C₃₃H₂₅N₇O₆
• 分子量: 615.605
• InChiKey: YIAVKHSWFZUJBX-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  161.56
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N²-acetyl-6-O-diphenylcarbamoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)guanosine 在 吡啶 、 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 26.33h， 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
• 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 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到N²-acetyl-6-O-diphenylcarbamoyl-9-(5'-O-benzoyl-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