(2-ethoxycarbonyl-ethyl)-phosphonic acid | 72563-46-3

• 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: (2-ethoxycarbonyl-ethyl)-phosphonic acid
• 英文别名: β-Phosphono-propionsaeure-C-aethylester；(2-Aethoxycarbonyl-aethyl)-phosphonsaeure；(3-Ethoxy-3-oxopropyl)phosphonic acid
• CAS: 72563-46-3
• 化学式: C₅H₁₁O₅P
• 分子量: 182.113
• InChiKey: AZHFBKAQVODQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-ethoxycarbonyl-ethyl)-phosphonic acid 、 N-acetyl-2',3'-di-O-acetylcytidine 在 吡啶 、 TIBS-Cl 作用下， 反应 15.0h， 生成 3-{[(2R,3R,4R,5R)-3,4-Diacetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-propionic acid ethyl ester
  参考文献：
  名称：

  New Potent Sialyltransferase Inhibitors—Synthesis of Donor and of Transition-State Analogues of Sialyl Donor CMP-Neu5Ac

  摘要：

  Enzymatic sialyl transfer with CMP-Neu5Ac as donor can be inhibited by CDP. Therefore phosphonates 1a,b, 2 and 3 were synthesized as substrate analogues. With alpha(2-6)-sialyltransferase from rat liver (EC2.4.99.1) only moderate inhibition was found for these compounds. In order to obtain transition-state analogues of CMP-Neu5Ac different linkages between 2,3-dehydro-N-acetylneuraminol and CMP were generated, yielding 4, (R)-5 and (R)-6. Compound (R)-6, in which the CMP residue is attached to C-1 of 2,3-dehydro-N-acetylneuramin-1-yl phosphonate, exhibited excellent alpha(2-6)-sialyltransferase inhibition in the nanomolar range (K-i=350 nM), resulting in a 130-fold higher affinity for the enzyme than CMP-Neu5Ac (K-M = 46 mu M).

  DOI：

  10.1002/(sici)1521-3765(19980615)4:6<1106::aid-chem1106>3.0.co;2-7
• 作为产物：
  描述：

  3-膦酰丙酸三乙脂 在 三甲基氯硅烷 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 (2-ethoxycarbonyl-ethyl)-phosphonic acid
  参考文献：
  名称：

  New Potent Sialyltransferase Inhibitors—Synthesis of Donor and of Transition-State Analogues of Sialyl Donor CMP-Neu5Ac

  摘要：

  Enzymatic sialyl transfer with CMP-Neu5Ac as donor can be inhibited by CDP. Therefore phosphonates 1a,b, 2 and 3 were synthesized as substrate analogues. With alpha(2-6)-sialyltransferase from rat liver (EC2.4.99.1) only moderate inhibition was found for these compounds. In order to obtain transition-state analogues of CMP-Neu5Ac different linkages between 2,3-dehydro-N-acetylneuraminol and CMP were generated, yielding 4, (R)-5 and (R)-6. Compound (R)-6, in which the CMP residue is attached to C-1 of 2,3-dehydro-N-acetylneuramin-1-yl phosphonate, exhibited excellent alpha(2-6)-sialyltransferase inhibition in the nanomolar range (K-i=350 nM), resulting in a 130-fold higher affinity for the enzyme than CMP-Neu5Ac (K-M = 46 mu M).

  DOI：

  10.1002/(sici)1521-3765(19980615)4:6<1106::aid-chem1106>3.0.co;2-7

文献信息

• Functional selectivity in phosphonate ester dealkylation with bromotrimethylsilane
  作者：Charles E. McKenna、John Schmidhuser

  DOI：10.1039/c39790000739

  日期：——

  Bromotrimethylsilane is highly selective for P–O silyldealkylation of mixed carboxylate–phosphonate alkyl esters and can be used to prepare trimethylsilyl amido-, alkynyl-, and iodoalkyl-phosphonates in good yield, thus making the corresponding phosphonic acids readily available via hydrolysis with neutral H2O.

  溴代三甲基硅烷对混合的羧酸酯-膦酸酯烷基酯的P-O甲硅烷基脱烷基化反应具有高度选择性，可用于制备三甲基硅烷基酰胺基，炔基和碘代烷基膦酸酯，收率很高，因此使相应的膦酸易于通过中性H水解获得2 O.
• Nylen, Chemische Berichte, 1926, vol. 59, p. 1122
  作者：Nylen

  DOI：——

  日期：——
• MCKENNA C. E.; SCHMIDHAUSER J., J. CHEM. SOC. CHEM. COMMUN., 1979, NO 17, 739
  作者：MCKENNA C. E.、 SCHMIDHAUSER J.

  DOI：——

  日期：——
• New Potent Sialyltransferase Inhibitors—Synthesis of Donor and of Transition-State Analogues of Sialyl Donor CMP-Neu5Ac
  作者：Franz Amann、Christoph Schaub、Bernd Müller、Richard R. Schmidt

  DOI：10.1002/(sici)1521-3765(19980615)4:6<1106::aid-chem1106>3.0.co;2-7

  日期：1998.6.15

  Enzymatic sialyl transfer with CMP-Neu5Ac as donor can be inhibited by CDP. Therefore phosphonates 1a,b, 2 and 3 were synthesized as substrate analogues. With alpha(2-6)-sialyltransferase from rat liver (EC2.4.99.1) only moderate inhibition was found for these compounds. In order to obtain transition-state analogues of CMP-Neu5Ac different linkages between 2,3-dehydro-N-acetylneuraminol and CMP were generated, yielding 4, (R)-5 and (R)-6. Compound (R)-6, in which the CMP residue is attached to C-1 of 2,3-dehydro-N-acetylneuramin-1-yl phosphonate, exhibited excellent alpha(2-6)-sialyltransferase inhibition in the nanomolar range (K-i=350 nM), resulting in a 130-fold higher affinity for the enzyme than CMP-Neu5Ac (K-M = 46 mu M).