dibenzyl (3(R),4-O-isopropylidene,2-oxobutyl) phosphonate | 343783-13-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dibenzyl (3(R),4-O-isopropylidene,2-oxobutyl) phosphonate
• 英文别名: dibenzyl {2-[(1R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxoethyl}phosphonate；2-bis(phenylmethoxy)phosphoryl-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone
• CAS: 343783-13-1
• 化学式: C₂₁H₂₅O₆P
• 分子量: 404.4
• InChiKey: GXYKPMADDOGKOM-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 sodium periodate 、 正丁基锂 、 溴 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 dibenzyl (3(R),4-O-isopropylidene,2-oxobutyl) phosphonate
  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

文献信息

• A Convenient Synthesis of Dibenzyl α,α-Difluoromethyl-β-ketophosphonates
  作者：Sylvain Ladame、Michèle Willson、Jacques Périé

  DOI：10.1002/1099-0690(200208)2002:15<2640::aid-ejoc2640>3.0.co;2-9

  日期：2002.8

  The first synthesis of dibenzyl α,α-difluoro-β-ketophosphonates has been accomplished by an original fluorination reaction, namely addition of the F+ ion to the enolate form of the corresponding dibenzyl β-ketophosphonate. After an easy cleavage of the benzyloxy protecting groups on the phosphorus atom, α-fluoro-β-ketophosphonic acids were subsequently obtained as stable carboxyphosphate mimics. This

  α,α-二氟-β-酮膦酸二苄酯的首次合成是通过原始氟化反应完成的，即将 F+ 离子加成到相应的 β-酮膦酸二苄酯的烯醇化物形式中。在磷原子上的苄氧基保护基团容易裂解后，随后获得 α-氟-β-酮膦酸作为稳定的羧基磷酸酯模拟物。这种方法能够将 α,α-二氟-β-酮膦酸酯部分引入多官能化分子中，从而使之前描述的二乙基膦酸酯路线不再适用。此外，对它们在中性和碱性条件下的稳定性的研究表明，酮-烯醇平衡在这些分子的分解途径中的重要性。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-d-glyceric acid (1,3-diPG) analogues
  作者：Sylvain Ladame、Michel Bardet、Jacques Périé、Michèle Willson

  DOI：10.1016/s0968-0896(00)00295-9

  日期：2001.3

  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.