P-(adamant-1-yl)-2',3'-dideoxyadenosine 5'-hydrogenphosphonate | 322684-80-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: P-(adamant-1-yl)-2',3'-dideoxyadenosine 5'-hydrogenphosphonate
• 英文别名: 9-[(2R,5S)-5-(1-adamantyloxyphosphonoyloxymethyl)oxolan-2-yl]purin-6-amine
• CAS: 322684-80-0
• 化学式: C₂₀H₂₈N₅O₄P
• 分子量: 433.447
• InChiKey: FKQKRDOGZPCKLV-SYIJETQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  P-(adamant-1-yl)-2',3'-dideoxyadenosine 5'-hydrogenphosphonate 在 potassium phosphate 作用下， 以 水 、 乙腈 为溶剂， 生成 3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester
  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：

  1-金刚烷醇 、 2',3'-dideoxyadenosine 5'-hydrogenphosphonate sodium salt 在 Dowex-50 (Py⁺) 、 吡啶 、 三甲基乙酰氯 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以73 mg的产率得到P-(adamant-1-yl)-2',3'-dideoxyadenosine 5'-hydrogenphosphonate
  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