Phosphoric acid dibenzyl ester 3-hydroxy-1-methyl-propyl ester | 142072-08-0

• 分子结构分类: 有机化合物
• 英文名称: Phosphoric acid dibenzyl ester 3-hydroxy-1-methyl-propyl ester
• 英文别名: dibenzyl 4-hydroxybutan-2-yl phosphate
• CAS: 142072-08-0
• 化学式: C₁₈H₂₃O₅P
• 分子量: 350.351
• InChiKey: ZEMOAOOOISUOTB-UHFFFAOYSA-N

物化性质

• 沸点：
  493.8±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  Phosphoric acid dibenzyl ester 1-methyl-3-triethylsilanyloxy-propyl ester 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以93%的产率得到Phosphoric acid dibenzyl ester 3-hydroxy-1-methyl-propyl ester
  参考文献：
  名称：

  A novel deacylation method using Grignard reagent without affecting the neighbouring base-sensitive functional groups

  摘要：

  研究表明，甲基和乙基格氏试剂可裂解苯甲酸酯和乙酸酯等酯官能团，而不会影响邻近的碱敏感官能团。

  DOI：

  10.1039/c39920000681

文献信息

• Selective phosphorylation of diols with a Lewis acid catalyst
  作者：Kyle A. Coppola、Joseph W. Testa、Emily E. Allen、Bianca R. Sculimbrene

  DOI：10.1016/j.tetlet.2014.05.047

  日期：2014.7

  We report a method for the Lewis acid catalyzed phosphorylation of dials with pyrophosphates. Titanium alkoxides were found to be effective catalysts in the selective mono-phosphorylation for a range of dials. Dials of varying chain lengths and substituents were screened, to study the factors that influence mono-versus di-phosphorylation. It was discovered that 2-alkyl-2-amino-1,3-propanediols can be selectively mono-phosphoiylated in up to 97% isolated yield. This structural core is mono-phosphorylated in numerous immunomodulating compounds including the FDA-approved drug, FTY720.[GRAPHICS](C) 2014 Elsevier Ltd. All rights reserved.