Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-amino-imidazol-1-yl)-tetrahydro-furan-3-yl ester | 917083-07-9

• 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: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-amino-imidazol-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 917083-07-9
• 化学式: C₁₄H₁₉N₃O₇
• 分子量: 341.321
• InChiKey: XBZGZTSDFSXRDF-FMKGYKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  131.97
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-(β-D-2,3,5-tri-O-acetylribofuranosyl)-4-nitroimidazole 在 palladium on activated charcoal 氢气 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-amino-imidazol-1-yl)-tetrahydro-furan-3-yl ester
  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