(+)-1-<(1R,3S,4R)-3-acetoxy-4-(acetoxymethyl)cyclopentyl>-5-ethyl-1H,3H-pyrimidin-2,4-dione | 173987-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (+)-1-<(1R,3S,4R)-3-acetoxy-4-(acetoxymethyl)cyclopentyl>-5-ethyl-1H,3H-pyrimidin-2,4-dione
• 英文别名: [(1R,2S,4R)-2-acetyloxy-4-(5-ethyl-2,4-dioxopyrimidin-1-yl)cyclopentyl]methyl acetate
• CAS: 173987-33-2
• 化学式: C₁₆H₂₂N₂O₆
• 分子量: 338.36
• InChiKey: FVWVMUKIDCBXOD-MCIONIFRSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-1-<(1R,3S,4R)-3-acetoxy-4-(acetoxymethyl)cyclopentyl>-5-ethyl-1H,3H-pyrimidin-2,4-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.67h， 以84%的产率得到Acetic acid (1S,2R,4R)-2-acetoxymethyl-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-cyclopentyl ester
  参考文献：
  名称：

  A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU

  摘要：

  A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a-carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.

  DOI：

  10.1080/15257779508010722
• 作为产物：
  描述：

  (3E)-1,1,1-trichloro-3-(ethoxymethylidene)pentan-2-one 在 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 ammonium hydroxide 、 三乙胺 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 水 、 甲苯 为溶剂， 反应 37.5h， 生成 (+)-1-<(1R,3S,4R)-3-acetoxy-4-(acetoxymethyl)cyclopentyl>-5-ethyl-1H,3H-pyrimidin-2,4-dione
  参考文献：
  名称：

  A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU

  摘要：

  A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a-carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.

  DOI：

  10.1080/15257779508010722