1-[(2R,5S)-5-(1-adamantyloxyphosphonoyloxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione | 322684-86-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-[(2R,5S)-5-(1-adamantyloxyphosphonoyloxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 322684-86-6
• 化学式: C₂₀H₂₇N₂O₆P
• 分子量: 422.418
• InChiKey: PAQIDGZQKBIUTR-NNKBYLESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,5S)-5-(1-adamantyloxyphosphonoyloxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 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 、 司他夫定 在 吡啶 、 三氯化磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以79%的产率得到1-[(2R,5S)-5-(1-adamantyloxyphosphonoyloxymethyl)-2,5-dihydrofuran-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

文献信息

• <i>P</i>-(Alkyl)-Nucleoside 5′-Hydrogenphosphonates as Depot Forms of Antiviral Nucleotide Analogues
  作者：A. L. Khandazhinskaya、E. A. Shirokova、I. L. Karpenko、N. F. Zakirova、N. B. Tarussova、A. A. Krayevsky

  DOI：10.1080/15257770008045461

  日期：2000.10

  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.