[(2R,3S,5R)-3-(10-azidodecoxymethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate | 155195-40-7

• 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: [(2R,3S,5R)-3-(10-azidodecoxymethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 155195-40-7
• 化学式: C₂₈H₃₉N₅O₇
• 分子量: 557.647
• InChiKey: BCPALFYBYYXANT-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-(10-azidodecoxymethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate 在 ammonium hydroxide 、 氨 、 三苯基膦 作用下， 以 甲醇 为溶剂， 生成 1-[(2R,4S,5R)-4-(10-aminodecoxymethoxy)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 3′-O-(ω-aminoalkoxymethyl)thymidine 5′-triphosphates, terminators of DNA synthesis that enable 3′-labelling

  摘要：

  Treatment of 5'-O-benzoylthymidine 1 with a mixture of acetic anhydride. acetic acid and dimethyl sulfoxide yielded 5'-O-benzoyl-3'-O-methylthiomethylthymidine 2, which was converted via the 3'-O-bromomethyl derivative into 3'-O-(omega-aminoalkoxymethyl)thymidines 7 bearing a 6, 8 or 10 methylene groups long hydrocarbon chain, and finally to their 5'-triphosphates 10. The latter compounds were shown to be terminators of DNA synthesis catalysed by thermostable Tet/z DNA-polymerase, and may be labelled at the aliphatic amino group with fluorescent probes.

  DOI：

  10.1039/p19940000211
• 作为产物：
  描述：

  10-溴-1-癸醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 lutidine 、 氯化铵 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 [(2R,3S,5R)-3-(10-azidodecoxymethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Synthesis of 3′-O-(ω-aminoalkoxymethyl)thymidine 5′-triphosphates, terminators of DNA synthesis that enable 3′-labelling

  摘要：

  Treatment of 5'-O-benzoylthymidine 1 with a mixture of acetic anhydride. acetic acid and dimethyl sulfoxide yielded 5'-O-benzoyl-3'-O-methylthiomethylthymidine 2, which was converted via the 3'-O-bromomethyl derivative into 3'-O-(omega-aminoalkoxymethyl)thymidines 7 bearing a 6, 8 or 10 methylene groups long hydrocarbon chain, and finally to their 5'-triphosphates 10. The latter compounds were shown to be terminators of DNA synthesis catalysed by thermostable Tet/z DNA-polymerase, and may be labelled at the aliphatic amino group with fluorescent probes.

  DOI：

  10.1039/p19940000211

文献信息

• Synthesis of 3′-O-(ω-aminoalkoxymethyl)thymidine 5′-triphosphates, terminators of DNA synthesis that enable 3′-labelling
  作者：Jari Hovinen、Elena Azhayeva、Alex Azhayev、Andrei Guzaev、Harri Lönberg

  DOI：10.1039/p19940000211

  日期：——

  Treatment of 5'-O-benzoylthymidine 1 with a mixture of acetic anhydride. acetic acid and dimethyl sulfoxide yielded 5'-O-benzoyl-3'-O-methylthiomethylthymidine 2, which was converted via the 3'-O-bromomethyl derivative into 3'-O-(omega-aminoalkoxymethyl)thymidines 7 bearing a 6, 8 or 10 methylene groups long hydrocarbon chain, and finally to their 5'-triphosphates 10. The latter compounds were shown to be terminators of DNA synthesis catalysed by thermostable Tet/z DNA-polymerase, and may be labelled at the aliphatic amino group with fluorescent probes.