5-[2,3,5-tri-O-acetyl-4-thio-β-D-ribofuranosyl]-2,4-dimethoxypyrimidine | 1335287-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-[2,3,5-tri-O-acetyl-4-thio-β-D-ribofuranosyl]-2,4-dimethoxypyrimidine
• 英文别名: [(2R,3S,4R,5S)-3,4-diacetyloxy-5-(2,4-dimethoxypyrimidin-5-yl)thiolan-2-yl]methyl acetate
• CAS: 1335287-43-8
• 化学式: C₁₇H₂₂N₂O₈S
• 分子量: 414.436
• InChiKey: CUKFBLCQOMMBEA-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-[2,3,5-tri-O-acetyl-4-thio-β-D-ribofuranosyl]-2,4-dimethoxypyrimidine 在 氨 、 sodium iodide 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 5-[4-thio-β-D-ribofuranosyl]uracil
  参考文献：
  名称：

  An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1-C-Aryl- or 1-C-Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome

  摘要：

  We have developed a novel method for the synthesis of the beta-anomer of 4'-thio-C-ribonucleosides from 3,5-O-(di-tert-butylsilylene)-4-thiofuranoid glycal. Palladium-catalyzed coupling of 1-tributylstannyl-4-thiofuranoid glycal with iodobenzene or a heteroaryl halide gave 1-C-phenyl- or 1-C-heteroaryl-glycals. Hydroboration of these glycals proceeded at the alpha-face, and subsequent alkaline hydrogen peroxide treatment of the resulting 2'-alpha-borane furnished the respective beta-anomer of 4'-thio-C-ribonucleosides. These results demonstrate that this synthetic method has a wider scope in terms of heterocyclic base structure. During this study, unexpected Markovnikov-oriented hydroboration has been observed to lead to the respective 1'-alpha-boranes. These 1'-boranes were converted into either the ring-opened structure or the 2'-deoxy derivatives depending upon their stability.

  DOI：

  10.1021/jo201100n
• 作为产物：
  描述：

  2,4-二甲氧基-5-碘嘧啶 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 双氧水 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 5-[2,3,5-tri-O-acetyl-4-thio-β-D-ribofuranosyl]-2,4-dimethoxypyrimidine
  参考文献：
  名称：

  An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1-C-Aryl- or 1-C-Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome

  摘要：

  We have developed a novel method for the synthesis of the beta-anomer of 4'-thio-C-ribonucleosides from 3,5-O-(di-tert-butylsilylene)-4-thiofuranoid glycal. Palladium-catalyzed coupling of 1-tributylstannyl-4-thiofuranoid glycal with iodobenzene or a heteroaryl halide gave 1-C-phenyl- or 1-C-heteroaryl-glycals. Hydroboration of these glycals proceeded at the alpha-face, and subsequent alkaline hydrogen peroxide treatment of the resulting 2'-alpha-borane furnished the respective beta-anomer of 4'-thio-C-ribonucleosides. These results demonstrate that this synthetic method has a wider scope in terms of heterocyclic base structure. During this study, unexpected Markovnikov-oriented hydroboration has been observed to lead to the respective 1'-alpha-boranes. These 1'-boranes were converted into either the ring-opened structure or the 2'-deoxy derivatives depending upon their stability.

  DOI：

  10.1021/jo201100n