methyl 3-azido-3-deoxy-β-D-xylofuranoside | 64623-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-3-deoxy-β-D-xylofuranoside
• 英文别名: (2R,3R,4R,5S)-4-azido-5-(hydroxymethyl)-2-methoxyoxolan-3-ol
• CAS: 64623-04-7
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: PLIZWGBKRRYANG-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-β-D-xylofuranoside 在 吡啶 、 potassium permanganate 、 偶氮二甲酸二异丙酯 、 苄基三乙基氯化铵 、 碳酸氢钠 、 三苯基膦 、 苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 methyl 2,5-anhydro-3-azido-3-deoxy-2-thio-β-D-lyxofuranoside 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-β-D-ribofuranoside de methyle 在 sodium azide 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 288.0h， 以74.5%的产率得到methyl 3-azido-3-deoxy-β-D-xylofuranoside
  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