1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-(N-methylenamino)-β-D-threo-pentofuranosyl>thymine N-oxide | 160989-30-0

• 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-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-(N-methylenamino)-β-D-threo-pentofuranosyl>thymine N-oxide
• 英文别名: 1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-(N-methylenamino)-β-D-threo-pentofuranosyl]thymine N-oxide
• CAS: 160989-30-0
• 化学式: C₁₇H₂₉N₃O₅Si
• 分子量: 383.52
• InChiKey: BVIABZVGAZCXGW-MGPQQGTHSA-N

物化性质

• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.39
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-(N-methylenamino)-β-D-threo-pentofuranosyl>thymine N-oxide 生成 1-<2,3-dideoxy-3-(N-hydroxyamino)-3-N,5-O-methano-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Anti-HIV Derivatives of 1-(2,3-Dideoxy-3-N-hydroxyamino-β-D-threo-pentofuranosyl)thymine

  摘要：

  Representative examples of the title compounds including bicyclic analogs (7-9) in which a perhydro-1,3-oxazine is ortho-fused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HIV-1 and HIV-2 replication in CEM cells (50% inhibitory concentration: 0.80-4.3 mu g/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these beta-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HIV active nucleosides bearing this configuration.

  DOI：

  10.1080/15257779408010670
• 作为产物：
  描述：

  1-<5'-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-(N-hydroxy-N-methylamino)-β-D-threo-pentofuranosyl>thymine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以57%的产率得到1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-3-(N-methylenamino)-β-D-threo-pentofuranosyl>thymine N-oxide
  参考文献：
  名称：

  Anti-HIV Derivatives of 1-(2,3-Dideoxy-3-N-hydroxyamino-β-D-threo-pentofuranosyl)thymine

  摘要：

  Representative examples of the title compounds including bicyclic analogs (7-9) in which a perhydro-1,3-oxazine is ortho-fused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HIV-1 and HIV-2 replication in CEM cells (50% inhibitory concentration: 0.80-4.3 mu g/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these beta-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HIV active nucleosides bearing this configuration.

  DOI：

  10.1080/15257779408010670