5-methyl-1-[(1S,2S,3S,4R)-2,3,5-tris-benzyloxy-1-ethylsulfanyl-4-hydroxy-pentyl]-1H-pyrimidine-2,4-dione | 1198760-94-9

• 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: 5-methyl-1-[(1S,2S,3S,4R)-2,3,5-tris-benzyloxy-1-ethylsulfanyl-4-hydroxy-pentyl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(1S,2S,3S,4R)-1-ethylsulfanyl-4-hydroxy-2,3,5-tris(phenylmethoxy)pentyl]-5-methylpyrimidine-2,4-dione
• CAS: 1198760-94-9
• 化学式: C₃₃H₃₈N₂O₆S
• 分子量: 590.741
• InChiKey: VBJFFMBRDXKBGU-GIGUTINRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methyl-1-[(1S,2S,3S,4R)-2,3,5-tris-benzyloxy-1-ethylsulfanyl-4-hydroxy-pentyl]-1H-pyrimidine-2,4-dione 在 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-(α-D-2',3',5'-tri-O-benzyl-lyxofuranosyl)thymine
  参考文献：
  名称：

  A Stereoselective Approach to Nucleosides and 4′-Thioanalogues from Acyclic Precursors

  摘要：

  D- and L-nucleosides and analogues thereof, including the 4'-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.

  DOI：

  10.1021/ja905452f
• 作为产物：
  描述：

  5-methyl-1-[(1S,2S,3R,4R)-2,3,5-tris-benzyloxy-4-(tert-butyl-dimethylsilanyloxy)-1-ethylsulfanyl-pentyl]-1H-pyrimidine-2,4-dione 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到5-methyl-1-[(1S,2S,3S,4R)-2,3,5-tris-benzyloxy-1-ethylsulfanyl-4-hydroxy-pentyl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  A Stereoselective Approach to Nucleosides and 4′-Thioanalogues from Acyclic Precursors

  摘要：

  D- and L-nucleosides and analogues thereof, including the 4'-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.

  DOI：

  10.1021/ja905452f

文献信息

• A Stereoselective Approach to Nucleosides and 4′-Thioanalogues from Acyclic Precursors
  作者：Daniel Chapdelaine、Benoit Cardinal-David、Michel Prévost、Marc Gagnon、Isabelle Thumin、Yvan Guindon

  DOI：10.1021/ja905452f

  日期：2009.12.2

  D- and L-nucleosides and analogues thereof, including the 4'-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.