dimethyl C-(2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)methanephosphonate | 223131-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl C-(2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)methanephosphonate
• 英文别名: (2S,3R,4R,5S)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-5-(dimethoxyphosphorylmethyl)-3,4-bis(phenylmethoxy)oxolane
• CAS: 223131-29-1
• 化学式: C₃₇H₄₃O₈P
• 分子量: 646.717
• InChiKey: UWSHZLTXIBQJLZ-GDWCTEMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl C-(2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)methanephosphonate 在 碘代三甲硅烷 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 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：

  2,3,5,6-tetra-O-benzyl-D-galactofuranose 在 正丁基锂 、 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 17.0h， 生成 dimethyl C-(2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)methanephosphonate
  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

文献信息

• <scp>d</scp>-Galactofuranosylphosphonates. First Synthesis of UDP-<i>C</i>-<scp>d</scp>-galactofuranose
  作者：José Kovensky、Michael McNeil、Pierre Sinaÿ

  DOI：10.1021/jo990196p

  日期：1999.8.1

  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.