dibenzyl (4-dibenzylphosphono,3-oxo,2(R)-hydroxybutyl) phosphate | 343783-15-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dibenzyl (4-dibenzylphosphono,3-oxo,2(R)-hydroxybutyl) phosphate
• CAS: 343783-15-3
• 化学式: C₃₂H₃₄O₉P₂
• 分子量: 624.564
• InChiKey: RCUAYHYLWVMOMZ-WJOKGBTCSA-N

物化性质

• 沸点：
  769.5±60.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  环己胺 、 dibenzyl (4-dibenzylphosphono,3-oxo,2(R)-hydroxybutyl) phosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到((R)-3-Hydroxy-2-oxo-4-phosphonooxy-butyl)-phosphonic acid; compound with cyclohexylamine
  参考文献：
  名称：

  Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-d-glyceric acid (1,3-diPG) analogues

  摘要：

  Various phosphono-phosphates and diphosphonates were synthesized as 1,3-diphosphoglycerate (1,3-diPG) analogues by using a beta -ketophosphonate, an alpha -fluoro,beta -ketophosphonate or a beta -ketophosphoramidate to mimic the unstable carboxyphosphate part of the natural substrate. The inhibitory effect of these analogues on glyceraldehyde-3-phosphate dehydrogenases (GAPDH) from Trypanosoma brucei (Tb) and rabbit muscle were measured with respect to both substrates, glyceraldehyde-3-phosphate (GAP) and 1,3-diPG. Interestingly, all 1,5-diphosphono,2-oxopentanes without substitution at the C-3 position selectively inhibit the Tb GAPDH with respect to 1,3-diPG and are without effect on Rm GAPDH. All 1-phospho,3-oxo,4-phosphonobutanes show themselves to be non-selective inhibitors either with regard to substrates or organisms, but they will be of a great interest as 1,3-diPG stable models for structural studies of co-crystals with GAPDHs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00295-9
• 作为产物：
  描述：

  dibenzyl (3(R),4-O-isopropylidene,2-oxobutyl) phosphonate 在 吡啶 、 盐酸 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 dibenzyl (4-dibenzylphosphono,3-oxo,2(R)-hydroxybutyl) phosphate
  参考文献：
  名称：

  Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-d-glyceric acid (1,3-diPG) analogues

  摘要：

  Various phosphono-phosphates and diphosphonates were synthesized as 1,3-diphosphoglycerate (1,3-diPG) analogues by using a beta -ketophosphonate, an alpha -fluoro,beta -ketophosphonate or a beta -ketophosphoramidate to mimic the unstable carboxyphosphate part of the natural substrate. The inhibitory effect of these analogues on glyceraldehyde-3-phosphate dehydrogenases (GAPDH) from Trypanosoma brucei (Tb) and rabbit muscle were measured with respect to both substrates, glyceraldehyde-3-phosphate (GAP) and 1,3-diPG. Interestingly, all 1,5-diphosphono,2-oxopentanes without substitution at the C-3 position selectively inhibit the Tb GAPDH with respect to 1,3-diPG and are without effect on Rm GAPDH. All 1-phospho,3-oxo,4-phosphonobutanes show themselves to be non-selective inhibitors either with regard to substrates or organisms, but they will be of a great interest as 1,3-diPG stable models for structural studies of co-crystals with GAPDHs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00295-9