(bromomethylethoxyphosphinoylmethyl)phosphonic acid diethyl ester | 911135-70-1

• 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: (bromomethylethoxyphosphinoylmethyl)phosphonic acid diethyl ester
• 英文别名: 1-[Bromomethyl(diethoxyphosphorylmethyl)phosphoryl]oxyethane；1-[bromomethyl(diethoxyphosphorylmethyl)phosphoryl]oxyethane
• CAS: 911135-70-1
• 化学式: C₈H₁₉BrO₅P₂
• 分子量: 337.087
• InChiKey: LHORAYMGZJNDHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (bromomethylethoxyphosphinoylmethyl)phosphonic acid diethyl ester 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 [(diethoxyphosphorylmethyl)ethoxyphosphinoylmethyl]phosphonic acid monomethyl ester
  参考文献：
  名称：

  An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues

  摘要：

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.

  DOI：

  10.1021/ol0615432
• 作为产物：
  描述：

  bis(bromomethyl)phosphinic acid ethyl ester 、 亚磷酸三乙酯 反应 2.5h， 以56%的产率得到(bromomethylethoxyphosphinoylmethyl)phosphonic acid diethyl ester
  参考文献：
  名称：

  An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues

  摘要：

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.

  DOI：

  10.1021/ol0615432

文献信息

• Bismethylene Triphosphate Nucleotides of Uridine 4-Phosphate Analogues:  A New Class of Anionic Pyrimidine Nucleotide Analogues
  作者：Scott D. Taylor、Farzad Mirzaei、Stephen L. Bearne

  DOI：10.1021/jo702249j

  日期：2008.2.1

  Cytidine-5‘-triphosphate synthase (CTPS) catalyzes the formation of cytidine triphosphate (CTP) from glutamine, uridine 5‘-triphosphate (UTP), and adenosine 5‘-triphosphate (ATP). This reaction proceeds via formation of the high-energy intermediate UTP-4-phosphate (UTP-4-P). Stable analogues of UTP-4-P may be potent inhibitors of CTPS and useful as lead structures for the development of anticancer

  胞嘧啶5'-三磷酸合酶（CTPS）催化由谷氨酰胺，尿苷5'-三磷酸（UTP）和腺苷5'-三磷酸（ATP）形成胞苷三磷酸（CTP）。该反应通过形成高能中间体UTP-4-磷酸盐（UTP-4-P）进行。UTP-4-P的稳定类似物可能是CTPS的有效抑制剂，可用作开发抗癌和抗病毒剂的先导结构。已经制备了尿苷4-磷酸酯（U-4-P）类似物的几个双亚甲基三磷酸酯（BMT）核苷酸。关键步骤是借助锡催化剂对2'，3'，5'-三-O-乙酰基或三-O的5'酯部分进行选择性甲醇分解-苯甲酰基U-4-P类似物。我们认为，这代表了在苯甲酰化核苷中选择性裂解5'苯甲酸酯的第一个通用方法。将这些5'-脱保护的U-4-P类似物与未对称的，受保护的BMT在末端位置之一上带有游离膦酸部分的Mitsunobu偶联，得到了完全保护的BMT-U-4-P类似物。使用TMSBr，然后用NH 4 OH-MeOH或NH 4 OH-吡啶处理
• An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues
  作者：Scott D. Taylor、Farzad Mirzaei、Stephen L. Bearne

  DOI：10.1021/ol0615432

  日期：2006.9

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.