methyl 5-S-acetyl-3-azido-3-deoxy-5-thio-α-D-xylofuranoside | 923600-24-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-S-acetyl-3-azido-3-deoxy-5-thio-α-D-xylofuranoside
• CAS: 923600-24-2
• 化学式: C₈H₁₃N₃O₄S
• 分子量: 247.275
• InChiKey: PAQIUHCTKWELHI-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  104.52
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 5-S-acetyl-3-azido-3-deoxy-5-thio-α-D-xylofuranoside 在 吡啶 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 methyl 2,5-anhydro-3-azido-3-deoxy-2-thio-α-D-lyxofuranoside
  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：

  硫代乙酸 、 2,3-anhydro-α-D-ribofuranoside de methyle 在 sodium azide 、 氯化铵 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 乙醇 、 四氢呋喃 为溶剂， 反应 88.0h， 以3.32 g的产率得到methyl 5-S-acetyl-2-azido-2-deoxy-5-thio-α-D-arabinofuranoside
  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