N1-(3-deoxy-3-C-dimethylphosphono-β-D-ribofuranosyl)-thymine | 161821-93-8

• 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-(3-deoxy-3-C-dimethylphosphono-β-D-ribofuranosyl)-thymine
• 英文别名: 1-[(2R,3S,4S,5R)-4-dimethoxyphosphoryl-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 161821-93-8
• 化学式: C₁₂H₁₉N₂O₈P
• 分子量: 350.265
• InChiKey: MSSHBZIXQMIZRA-TURQNECASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N1-(3-deoxy-3-C-dimethylphosphono-β-D-ribofuranosyl)-thymine 在 吡啶 、 三甲基溴硅烷 、 水 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 N1-(2-hydroxy-3-deoxy-3-C-dihydroxyphosphono-β-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
• 作为产物：
  描述：

  1,2-di-O-acetyl-3-deoxy-3-C-dimethylphosphono-5-O-benzoyl-α-D-ribofuranose 在 三甲基氯硅烷 、 sodium methylate 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.08h， 生成 N1-(3-deoxy-3-C-dimethylphosphono-β-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.