4-N-[(S)-pyrrolidine-2-carbonyl]amino-1-β-D-ribofuranosylimidazole

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 4-N-[(S)-pyrrolidine-2-carbonyl]amino-1-β-D-ribofuranosylimidazole
• 英文别名: (2S)-N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl]pyrrolidine-2-carboxamide
• 化学式: C₁₃H₂₀N₄O₅
• 分子量: 312.326
• InChiKey: BHWTUSLXFAKTAG-WMNYDERDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-amino-imidazol-1-yl)-tetrahydro-furan-3-yl ester 在 palladium on activated charcoal 氨 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 4-N-[(S)-pyrrolidine-2-carbonyl]amino-1-β-D-ribofuranosylimidazole
  参考文献：
  名称：

  Synthesis of Ribavirin Analogues Containing Amino‐Acid Residues

  摘要：

  A convenient procedure for coupling 1,2,3,5-tetra-O-acetyl-,beta-D-ribofuranose and 4-nitroimidazole was developed to obtain beta-anomer as the major product. A novel category of nucleoside analogues with the introduction of natural L-amino acids to the base moiety were designed and synthesized to develop selective and effective antiviral agents.

  DOI：

  10.1081/scc-200054185

文献信息

• Synthesis of Ribavirin Analogues Containing Amino‐Acid Residues
  作者：Daliang Li、Hongli Bao、Qitao Tan、Dongmei Cai、Tianpa You

  DOI：10.1081/scc-200054185

  日期：2005.4.1

  A convenient procedure for coupling 1,2,3,5-tetra-O-acetyl-,beta-D-ribofuranose and 4-nitroimidazole was developed to obtain beta-anomer as the major product. A novel category of nucleoside analogues with the introduction of natural L-amino acids to the base moiety were designed and synthesized to develop selective and effective antiviral agents.