methyl-5-(2)H-3,5-O-bis-p-toluoyl-2-α,β-D-erythro-pentofuranoside | 1239990-48-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-5-(2)H-3,5-O-bis-p-toluoyl-2-α,β-D-erythro-pentofuranoside
• CAS: 1239990-48-7
• 化学式: C₂₂H₂₄O₆
• 分子量: 385.421
• InChiKey: MTMWQYDEGWXCTH-ZIDKFIBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl-5-(2)H-3,5-O-bis-p-toluoyl-2-α,β-D-erythro-pentofuranoside 在 盐酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到(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
• 作为产物：
  描述：

  在 吡啶 、 N-甲基咪唑 、 B-3-pinanyl-9-borabicyclo[3.3.1]nonane 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 methyl-5-(2)H-3,5-O-bis-p-toluoyl-2-α,β-D-erythro-pentofuranoside
  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