[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-chloro-5-cyano-3-methyl-4-oxopyrrolo[2,3-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate | 191924-03-5

• 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: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-chloro-5-cyano-3-methyl-4-oxopyrrolo[2,3-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate
• CAS: 191924-03-5
• 化学式: C₁₉H₁₉ClN₄O₈
• 分子量: 466.835
• InChiKey: DJTARMFEXCACKM-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  151.74
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-chloro-5-cyano-3-methyl-4-oxopyrrolo[2,3-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate 在 氨 作用下， 反应 18.0h， 以96.9%的产率得到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
• 作为产物：
  描述：

  5-cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 在 二环己烷并-18-冠醚-6 、 potassium fluoride 、 sodium nitrite 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 35.0h， 生成 [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-chloro-5-cyano-3-methyl-4-oxopyrrolo[2,3-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate
  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