dibenzyl (3-hydroxypropyl) phosphate

• 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 (3-hydroxypropyl) phosphate
• 英文别名: Dibenzyl 3-hydroxypropyl phosphate；dibenzyl 3-hydroxypropyl phosphate
• 化学式: C₁₇H₂₁O₅P
• 分子量: 336.324
• InChiKey: IJQAOPVRDGZHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dibenzyl (3-hydroxypropyl) phosphate 、 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  PHOSPHATE PRODRUGS OF CANNABINOIDS

  摘要：

  Phosphate prodrugs of cannabinoids, with enhanced physicochemical, pharmacological, and/or pharmacokinetic properties, such as enhanced aqueous solubility and enhanced oral bioavailability are disclosed herein, as are pharmaceutical compositions comprising one or more of the same. Such compounds and compositions are useful for the treatment of diseases, disorders, and/or conditions where treatment with a cannabinoid may be useful, including pain, multiple sclerosis, and epilepsy.

  公开号：

  WO2024163803A1
• 作为产物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 dibenzyl (3-hydroxypropyl) phosphate
  参考文献：
  名称：

  [EN] NEW SPIROCYCLOHEXANE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USES AS ANTI-APOPTOTIC INHIBITORS
  [FR] NOUVEAUX DÉRIVÉS DE SPIROCYCLOHEXANE, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET LEURS UTILISATIONS COMME INHIBITEURS ANTI-APOPTOTIQUES

  摘要：

  式 (I) 的化合物：其中 R1、R2、R3、R4 和如描述中所定义。药物。

  公开号：

  WO2024008941A1

文献信息

• Direct mono-phosphorylation of 1,3-diols. A synthesis of FTY720-phosphate
  作者：Shuzo Takeda、Masao Chino、Masatoshi Kiuchi、Kunitomo Adachi

  DOI：10.1016/j.tetlet.2005.05.127

  日期：2005.8

  A novel method for selective and direct phosphorylation of various 1,3-diols using silver(I) oxide, tetrabenzyl pyrophosphate (TBPP), and tetrahexylammonium iodide affording mono-phosphates was developed. We applied the present method to the synthesis of FTY720-phosphate.

  提出了一种使用氧化银（I），焦磷酸四苄基酯（TBPP）和碘化四己基碘化铵选择性和直接磷酸化各种1,3-二醇的方法，从而提供了单磷酸酯。我们将本方法应用于FTY720-磷酸酯的合成。
• Prodrug Strategies to Improve the Solubility of the HCV NS5A Inhibitor Pibrentasvir (ABT-530)
  作者：John T. Randolph、Eric A. Voight、Stephen N. Greszler、Brice E. Uno、James N. Newton、Kenneth M. Gleason、DeAnne Stolarik、Cecilia Van Handel、Daniel A. J. Bow、David A. DeGoey

  DOI：10.1021/acs.jmedchem.0c00956

  日期：2020.10.8

  A research program to discover solubilizing prodrugs of the HCV NS5A inhibitor pibrentasvir (PIB) identified phosphomethyl analog 2 and trimethyl-lock (TML) prodrug 9. The prodrug moiety is attached to a benzimidazole nitrogen atom via an oxymethyl linkage to allow for rapid and complete release of the drug for absorption following phosphate removal by intestinal alkaline phosphatase. These prodrugs have good hydrolytic stability properties and improved solubility compared to PIB, both in aqueous buffer (pH 7) and FESSIF (pH 5). TML prodrug 9 provided superior in vivo performance, delivering high plasma concentrations of PIB in PK studies conducted in mice, dogs, and monkeys. The improved dissolution properties of these phosphate prodrugs provide them the potential to simplify drug dosage forms for PIB-containing HCV therapy.
• 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.