1(1-cyano-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thymine | 152039-42-4

• 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: 1(1-cyano-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thymine
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-cyano-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 152039-42-4
• 化学式: C₃₂H₂₅N₃O₉
• 分子量: 595.565
• InChiKey: ZBVMVPSQMDKUEK-WRZBRUQPSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1(1-cyano-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thymine 在 咪唑 、 ammonium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1(5-O-tert-butyldimethylsilyl-1-cyano-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and structure determination of the first 1′-C-cyano-β-D-nucleosides

  摘要：

  The 1'-cyano -2',3'-D-unsaturated nucleoside 8 was synthesised according to the following steps. Photobromination of the ribofuranosyl cyanide 1 using N-bromosuccinimide (NBS) as a radical source gave the two isomers of the new C-1 gem disubstituted sugar 2. Its condensation with silylated thymine afforded the blocked nucleoside 3, the stereochemistry and molecular shape of which were deduced from NMR studies and molecular simulation. After deprotection of 3 into 4, thiocarbonylation of the silylated derivative 5, followed by olefination of 6, led to 7 which was deblocked to the 1'-cyano substituted d4T 8.

  DOI：

  10.1016/s0040-4020(01)96264-7
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-1-bromo-D-ribofuranosyl cyanide 、 O,O-二(三甲基甲硅烷基)胸苷 在 氰化汞 作用下， 以 硝基甲烷 为溶剂， 反应 72.0h， 以56%的产率得到1(1-cyano-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and structure determination of the first 1′-C-cyano-β-D-nucleosides

  摘要：

  The 1'-cyano -2',3'-D-unsaturated nucleoside 8 was synthesised according to the following steps. Photobromination of the ribofuranosyl cyanide 1 using N-bromosuccinimide (NBS) as a radical source gave the two isomers of the new C-1 gem disubstituted sugar 2. Its condensation with silylated thymine afforded the blocked nucleoside 3, the stereochemistry and molecular shape of which were deduced from NMR studies and molecular simulation. After deprotection of 3 into 4, thiocarbonylation of the silylated derivative 5, followed by olefination of 6, led to 7 which was deblocked to the 1'-cyano substituted d4T 8.

  DOI：

  10.1016/s0040-4020(01)96264-7