O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate | 244642-03-3

• 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: O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-(phenylmethoxyphosphonoyloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 244642-03-3
• 化学式: C₁₇H₂₀N₅O₆P
• 分子量: 421.349
• InChiKey: PWKZIKUUDHVIGR-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate 在 吡啶 、 potassium phosphate 、 三甲基乙酰氯 、 三氯化磷 作用下， 以 二氯甲烷 、 水 、 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：

  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 O-benzyl-O'-(3'-azido-3'-deoxythymidin-5'-yl) phosphonate
  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

• Synthesis of AZT/d4T Boranophosphates as Anti-HIV Prodrug Candidates
  作者：Hua Fu、Yufen Zhao、Changxue Lin、Guangzhong Tu

  DOI：10.1055/s-2004-815939

  日期：——

  AZT/d4T phosphonates were synthesized by sequential condensation of AZT/d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

  AZT/d4T膦酸盐是通过在异戊酰氯存在下，依次将AZT/d4T与相应的醇或5′-DMT胸苷缩合合成的。这些膦酸盐依次进行硅烷化、硼化及在氨水中水解，得到抗HIV前药候选物AZT/d4T硼膦酸盐。
• Sun, Xiao Bin; Kang, Jian Xun; Zhao, Yu Fen, Chemical Communications, 2002, # 20, p. 2414 - 2415
  作者：Sun, Xiao Bin、Kang, Jian Xun、Zhao, Yu Fen

  DOI：——

  日期：——