aza-D4T | 334024-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: aza-D4T
• 英文别名: aza-stavudine；tert-butyl (2S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydropyrrole-1-carboxylate
• CAS: 334024-83-8
• 化学式: C₁₅H₂₁N₃O₅
• 分子量: 323.349
• InChiKey: OORFNXFMWITSKE-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  aza-D4T 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以92%的产率得到aza-DDT
  参考文献：
  名称：

  Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate

  摘要：

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02343-1
• 作为产物：
  描述：

  5-甲基-1,3-二(三甲基硅烷基)-2,4(1H,3H)-嘧啶二酮 在 双氧水 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 aza-D4T
  参考文献：
  名称：

  Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate

  摘要：

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02343-1