Benzoic acid (2R,3S,5R)-3-(8-bromo-octyloxymethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 1053727-25-5

• 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: Benzoic acid (2R,3S,5R)-3-(8-bromo-octyloxymethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3S,5R)-3-(8-bromooctoxymethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 1053727-25-5
• 化学式: C₂₆H₃₅BrN₂O₇
• 分子量: 567.477
• InChiKey: JWFFFXWFHCOXOA-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S,5R)-3-(8-bromo-octyloxymethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 ammonium hydroxide 、 sodium azide 、 氨 、 氯化铵 、 三苯基膦 、 lithium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(2R,4S,5R)-4-(8-Amino-octyloxymethoxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-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：

  5'-benzoylthymidine 在 N-溴代丁二酰亚胺(NBS) 、 lutidine 、 乙酸酐 、 溶剂黄146 作用下， 反应 48.17h， 生成 Benzoic acid (2R,3S,5R)-3-(8-bromo-octyloxymethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  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