Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-(8-methoxy-2-oxido-4H-1,3,2-benzodioxaphosphorin-2-yl)- | 201165-99-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-(8-methoxy-2-oxido-4H-1,3,2-benzodioxaphosphorin-2-yl)-
• 英文别名: 1-[(2R,5S)-5-[(8-methoxy-2-oxo-4H-1,3,2λ5-benzodioxaphosphinin-2-yl)oxymethyl]-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 201165-99-3
• 化学式: C₁₈H₁₉N₂O₈P
• 分子量: 422.331
• InChiKey: FMJGZLFHGBFKTH-BUEPIDKJSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-(8-methoxy-2-oxido-4H-1,3,2-benzodioxaphosphorin-2-yl)- 以 水 为溶剂， 生成 2-羟基-3-甲氧基苄醇 、 3'-deoxy-2',3'-didehydro-5'-O-dihydroxyphosphoryl thymidine
  参考文献：
  名称：

  Cyclo-saligenyl-2′,3′-dideoxy-2′,3′-didehydroythymidinemonophosphate (cycloSal-d4TMP) — A New Pro-Nucleotide Approach

  摘要：

  The synthesis of cycloSal-d4TMP 3a-g as new pro-nucleotide approach for d4TMP 2 is described. Phosphotriesters 3 release the d4TMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSal-phosphotriesters 3 exhibited high biological activity against HIV-1/HIV-2 in CEM cells which was completely retained in CEM TK- cells.

  DOI：

  10.1080/07328319708006176
• 作为产物：
  描述：

  3-甲氧基水杨酸 在 吡啶 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 2.83h， 生成 Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-(8-methoxy-2-oxido-4H-1,3,2-benzodioxaphosphorin-2-yl)-
  参考文献：
  名称：

  Cyclo-saligenyl-2′,3′-dideoxy-2′,3′-didehydroythymidinemonophosphate (cycloSal-d4TMP) — A New Pro-Nucleotide Approach

  摘要：

  The synthesis of cycloSal-d4TMP 3a-g as new pro-nucleotide approach for d4TMP 2 is described. Phosphotriesters 3 release the d4TMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSal-phosphotriesters 3 exhibited high biological activity against HIV-1/HIV-2 in CEM cells which was completely retained in CEM TK- cells.

  DOI：

  10.1080/07328319708006176