1-[(2R,4S,5S)-4-azido-5-(2,2-dimethylpropoxyphosphonoyloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 376356-94-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,4S,5S)-4-azido-5-(2,2-dimethylpropoxyphosphonoyloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 376356-94-4
• 化学式: C₁₅H₂₄N₅O₆P
• 分子量: 401.359
• InChiKey: GXJBEAAJWHHQAD-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5S)-4-azido-5-(2,2-dimethylpropoxyphosphonoyloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 三甲基乙酰氯 、 三氯化磷 作用下， 以 二氯甲烷 、 formamide 、 乙腈 为溶剂， 反应 3.0h， 生成 1-[(2R,4S,5S)-5-(1-adamantyloxyphosphonoyloxymethyl)-4-azidooxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  P-(Alkyl)-Nucleoside 5′-Hydrogenphosphonates as Depot Forms of Antiviral Nucleotide Analogues

  摘要：

  P-(Alkyl)esters of AZT 5'-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded, AZT 5'-hydrogenphosphonate. The corresponding derivatives of d2A and d4T showed the same properties.

  DOI：

  10.1080/15257770008045461
• 作为产物：
  描述：

  O-cyclohexyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 在 吡啶 、 potassium phosphate 、 三氯化磷 作用下， 以 二氯甲烷 、 水 、 formamide 、 乙腈 为溶剂， 生成 1-[(2R,4S,5S)-4-azido-5-(2,2-dimethylpropoxyphosphonoyloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  P-(Alkyl)-Nucleoside 5′-Hydrogenphosphonates as Depot Forms of Antiviral Nucleotide Analogues

  摘要：

  P-(Alkyl)esters of AZT 5'-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded, AZT 5'-hydrogenphosphonate. The corresponding derivatives of d2A and d4T showed the same properties.

  DOI：

  10.1080/15257770008045461