(2R,3S,5R)-5-chloro-2-((R)-((4-methylbenzoyl)oxy)methyl-d)tetrahydrofuran-3-yl 4-methylbenzoate | 1239990-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,5R)-5-chloro-2-((R)-((4-methylbenzoyl)oxy)methyl-d)tetrahydrofuran-3-yl 4-methylbenzoate
• CAS: 1239990-49-8
• 化学式: C₂₁H₂₁ClO₅
• 分子量: 389.84
• InChiKey: FJHSYOMVMMNQJQ-KFZXVRLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-chloro-2-((R)-((4-methylbenzoyl)oxy)methyl-d)tetrahydrofuran-3-yl 4-methylbenzoate 在 甲醇 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Stereoselective Nucleoside Deuteration for NMR Studies of DNA

  摘要：

  A procedure has been elaborated for stereoselective deuterium substitution of one of the diastereotopic 5'-protons in 2'-deoxynucleotides. The synthetic scheme uses the reduction of the 5-oxosugar derivative with deuterated Alpine-Borane. The resulting deuterosugar is converted into pyrimidine nucleosides and incorporated into DNA using standard protocols. Comparison of two-dimensional NMR spectra of the fully protonated and partially deuterated duplexes allowed us to assign diastereotopic 5' protons, increasing the number of experimental restraints used for structure determination.

  DOI：

  10.1080/15257770.2010.494650
• 作为产物：
  描述：

  在 吡啶 、 N-甲基咪唑 、 盐酸 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2R,3S,5R)-5-chloro-2-((R)-((4-methylbenzoyl)oxy)methyl-d)tetrahydrofuran-3-yl 4-methylbenzoate
  参考文献：
  名称：

  Stereoselective Nucleoside Deuteration for NMR Studies of DNA

  摘要：

  A procedure has been elaborated for stereoselective deuterium substitution of one of the diastereotopic 5'-protons in 2'-deoxynucleotides. The synthetic scheme uses the reduction of the 5-oxosugar derivative with deuterated Alpine-Borane. The resulting deuterosugar is converted into pyrimidine nucleosides and incorporated into DNA using standard protocols. Comparison of two-dimensional NMR spectra of the fully protonated and partially deuterated duplexes allowed us to assign diastereotopic 5' protons, increasing the number of experimental restraints used for structure determination.

  DOI：

  10.1080/15257770.2010.494650