methyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside | 18685-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside
• 英文别名: Methyl-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosid)；(2S,3S,4R,5R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-5-methoxy-3,4-bis(phenylmethoxy)oxolane
• CAS: 18685-21-7
• 化学式: C₃₅H₃₈O₆
• 分子量: 554.683
• InChiKey: MUEQYWXHSGXLFO-NDFHSCBSSA-N

物化性质

• 沸点：
  658.3±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside 在 正丁基锂 、 碘代三甲硅烷 、 硫酸 、 碘 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 正己烷 、 水 为溶剂， 反应 19.5h， 生成 C-(1-deoxy-α-D-galactofuranosyl)methanephosphonic acid
  参考文献：
  名称：

  d-Galactofuranosylphosphonates. First Synthesis of UDP-C-d-galactofuranose

  摘要：

  The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the cr-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP-galactopyranose mutase crystallization studies.

  DOI：

  10.1021/jo990196p
• 作为产物：
  描述：

  Methyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside 在 sodium 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  d-Galactofuranosylphosphonates. First Synthesis of UDP-C-d-galactofuranose

  摘要：

  The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the cr-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP-galactopyranose mutase crystallization studies.

  DOI：

  10.1021/jo990196p