1-((1S,3S,4S,7S)-7-Azido-2-oxa-5-thia-bicyclo[2.2.1]hept-3-yl)-5-methyl-1H-pyrimidine-2,4-dione | 923600-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((1S,3S,4S,7S)-7-Azido-2-oxa-5-thia-bicyclo[2.2.1]hept-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 923600-36-6
• 化学式: C₁₀H₁₁N₅O₃S
• 分子量: 281.295
• InChiKey: PBEXACSGTIZNFJ-XKBZYTNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  112.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-((1S,3S,4S,7S)-7-Azido-2-oxa-5-thia-bicyclo[2.2.1]hept-3-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以73.8%的产率得到1-(2,5-anhydro-3-azido-3-deoxy-2-thio-α-D-lyxofyranosyl)thymine (S)-S-oxide
  参考文献：
  名称：

  Synthesis and Reactions of Anhydro-Azido-thio-D-lyxofuranosides

  摘要：

  2,5-anhydro-3-azido-2-thio-D-lyxofuranosides and 3,5-anhydro-2-azido-3-thio-D-lyxofuranosides were prepared from methyl D-xylofuranoside or methyl D-ribofuranoside via corresponding 2,3-epoxysugars or the 5-O-trityl derivative. The sulfur was introduced into molecules by use of the thio-Mitsunobu reaction. Bicyclic azido-thiosugars were transformed into nucleoside analogues, oxidized to sulfoxides and sulfones, and reduced to bicyclic amino-thiosugars. Structures and configurations of products were determined by NMR spectroscopy or X-ray structure analyses.

  DOI：

  10.1080/10426500500326545
• 作为产物：
  描述：

  2,3-anhydro-α-D-ribofuranoside de methyle 在 吡啶 、 硫酸氢铵 、 sodium azide 、 碳酸氢钠 、 氯化铵 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 109.0h， 生成 1-((1S,3S,4S,7S)-7-Azido-2-oxa-5-thia-bicyclo[2.2.1]hept-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Reactions of Anhydro-Azido-thio-D-lyxofuranosides

  摘要：

  2,5-anhydro-3-azido-2-thio-D-lyxofuranosides and 3,5-anhydro-2-azido-3-thio-D-lyxofuranosides were prepared from methyl D-xylofuranoside or methyl D-ribofuranoside via corresponding 2,3-epoxysugars or the 5-O-trityl derivative. The sulfur was introduced into molecules by use of the thio-Mitsunobu reaction. Bicyclic azido-thiosugars were transformed into nucleoside analogues, oxidized to sulfoxides and sulfones, and reduced to bicyclic amino-thiosugars. Structures and configurations of products were determined by NMR spectroscopy or X-ray structure analyses.

  DOI：

  10.1080/10426500500326545