methyl-3,5-di-O-benzyl-2-O-(prop-2-ynyl)-α-D-xylofuranose | 1612222-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-3,5-di-O-benzyl-2-O-(prop-2-ynyl)-α-D-xylofuranose
• 英文别名: (2S,3R,4S,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)-3-prop-2-ynoxyoxolane
• CAS: 1612222-33-9
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: HYLJLMAWGFWHOQ-ACESQOTJSA-N

物化性质

• 沸点：
  510.0±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl-3,5-di-O-benzyl-2-O-(prop-2-ynyl)-α-D-xylofuranose 在 sodium azide 、 Cu*O₄S^(2-)*5H₂O 、 sodium hydride 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成
  参考文献：
  名称：

  Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

  摘要：

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.

  DOI：

  10.1021/jo500890w
• 作为产物：
  描述：

  1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 methyl-3,5-di-O-benzyl-2-O-(prop-2-ynyl)-α-D-xylofuranose
  参考文献：
  名称：

  Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

  摘要：

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.

  DOI：

  10.1021/jo500890w