N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-α-D-ribofuranosyl)-thymine

• 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: N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-α-D-ribofuranosyl)-thymine
• 英文别名: [(2R,3S,5S)-3-dimethoxyphosphoryl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• 化学式: C₁₉H₂₃N₂O₈P
• 分子量: 438.374
• InChiKey: NWNWGBWTNVOVRC-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  胸腺嘧啶 、 1-O-methyl-2,3-dideoxy-3-(RS)-C-dimethylphosphono-5-O-benzoyl-αβ-D-furanose 在 硫酸氢铵 、 四氯化锡 、 六甲基二硅氮烷 作用下， 生成 N1-(2,3-dideoxy-3-(R)-C-dimethylphosphono-5-O-benzoyl-α-D-ribofuranosyl)-thymine 、 N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine 、 N1-(2,3-dideoxy-3-(R)-C-dimethylphosphono-5-O-benzoyl-β-D-ribofuranosyl)-thymine 、 N1-(2,3-dideoxy-3-(S)-C-dimethylphosphono-5-O-benzoyl-α-D-ribofuranosyl)-thymine
  参考文献：
  名称：

  3′-C-phosphonates as nucleotides analogues synthesis starting from original C-phosphonosugars (in ribo- and deoxyribo- series)

  摘要：

  3-C-phosphonosugars were synthetised starting from 2-deoxy-D-ribose and alpha-D-xylofuranose via the Pudovic reaction followed by reduction. Their condensation with nucleobases (thymine and adenine) gave original 3'-C-phosphononucleosides in ribo- and 2-deoxyribo- series, with a stereocontrol of the reactions.

  DOI：

  10.1016/s0040-4020(01)85564-2

文献信息

• 3′-C-phosphonates as nucleotides analogues synthesis starting from original C-phosphonosugars (in ribo- and deoxyribo- series)
  作者：Corine Serra、Georges Dewynter、Jean-Louis Montero、Jean-Louis Imbach

  DOI：10.1016/s0040-4020(01)85564-2

  日期：1994.1

  3-C-phosphonosugars were synthetised starting from 2-deoxy-D-ribose and alpha-D-xylofuranose via the Pudovic reaction followed by reduction. Their condensation with nucleobases (thymine and adenine) gave original 3'-C-phosphononucleosides in ribo- and 2-deoxyribo- series, with a stereocontrol of the reactions.