2-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile | 191924-04-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 2-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 191924-04-6
• 化学式: C₁₃H₁₅N₅O₅
• 分子量: 321.293
• InChiKey: FGIJYHDWJBTRQF-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  159.55
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以26%的产率得到
  参考文献：
  名称：

  Synthesis of Pyrrolo[2,3-d]pyrimidines that are Structurally Related to Methylated Guanosines from tRNA and the Nucleoside Q Analogs, PreQ₀and PreQ₁

  摘要：

  The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5-cyano-2,4-dichloro-7-(2,3,5-tri-(O>$) over bar under bar>-acetyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (10) These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.

  DOI：

  10.1080/07328319708001355
• 作为产物：
  描述：

  [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-chloro-5-cyano-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate 在 potassium fluoride 、 氨 作用下， 以 乙腈 为溶剂， 反应 33.0h， 生成 2-Amino-7-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of Pyrrolo[2,3-d]pyrimidines that are Structurally Related to Methylated Guanosines from tRNA and the Nucleoside Q Analogs, PreQ₀and PreQ₁

  摘要：

  The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5-cyano-2,4-dichloro-7-(2,3,5-tri-(O>$) over bar under bar>-acetyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (10) These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.

  DOI：

  10.1080/07328319708001355