1-<<4(S),5-dihydroxy-1-(dimethylphosphonyl)-3(R)-pentoxy>methyl>thymine | 174359-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-<<4(S),5-dihydroxy-1-(dimethylphosphonyl)-3(R)-pentoxy>methyl>thymine
• 英文别名: 1-[[(2S,3R)-5-dimethoxyphosphoryl-1,2-dihydroxypentan-3-yl]oxymethyl]-5-methylpyrimidine-2,4-dione
• CAS: 174359-01-4
• 化学式: C₁₃H₂₃N₂O₈P
• 分子量: 366.308
• InChiKey: NCHHRCNSXZVFGB-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-<<4(S),5-dihydroxy-1-(dimethylphosphonyl)-3(R)-pentoxy>methyl>thymine 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到1-<<4(S),5-dihydroxy-1-phosphonyl-3(R)-pentoxy>methyl>thymine
  参考文献：
  名称：

  Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides

  摘要：

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.

  DOI：

  10.1021/jo951701v
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 palladium dihydroxide 、 乙醇 、 四乙基碘化铵 、 环己烯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-<<4(S),5-dihydroxy-1-(dimethylphosphonyl)-3(R)-pentoxy>methyl>thymine
  参考文献：
  名称：

  Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides

  摘要：

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.

  DOI：

  10.1021/jo951701v

文献信息

• Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides
  作者：Hussein I. El-Subbagh、Saibaba Racha、Elie Abushanab、Raymond P. Panzica

  DOI：10.1021/jo951701v

  日期：1996.1.1

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.