157547-58-5

Upstream product

• 110-63-4 Butane-1,4-diol 
• 67746-43-4 dibenzyl N,N-diethylphosphoramidite 
• 990-91-0 dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate 
• 1383382-43-1 dibenzyl 4-acetatebutyl phosphate 
• 157547-57-4 1-(Dibenzylphosphonooxy)-4-(t-butyldimethylsilyloxy)butane 

Downstream Products

• 170436-95-0 4-(dibenzylphosphonooxy)butyl 1H-imidazole-1-carboxylate 
• 157547-59-6 4-{[bis(benzyloxy)phosphoryl]oxy}butanoic acid 
• 1383382-46-4 4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutyl dibenzyl phosphate 
• 1383382-45-3 dibenzyl 4-oxobutyl phosphate 

Relevant academic research and scientific papers

Prodrug Strategies to Improve the Solubility of the HCV NS5A Inhibitor Pibrentasvir (ABT-530)

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

We report a method for the Lewis acid catalyzed phosphorylation of diols with pyrophosphates. Titanium alkoxides were found to be effective catalysts in the selective mono-phosphorylation for a range of diols. Diols 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-phosphorylated in up to 97% isolated yield. This structural core is mono-phosphorylated in numerous immunomodulating compounds including the FDA-approved drug, FTY720.

PROTEIN AFFINITY TAG AND USES THEREOF

This invention concerns isotopically coded or non-isotopically coded affinity-tags for analysis of certain target molecules in complex samples, in particular for mass spectrometric analysis of proteomic samples. The affinity-tags have the following general formula X-SPACER-OPO3H2, wherein X is a functional group or moiety capable of reacting with a functional group of a protein, peptide, DNA, lipid, sugar and/or steroid. These phosphate affinity tags (‘PTAG’) are capable of high but reversible binding to metal-oxides like TiO2. Due to this property, tagged sample fractions can be isolated from non-tagged sample fraction by affinity chromatography. The binding of organophosphate to metal-oxides remains intact during multiple washings of preferably acidic solutions to remove non-specifically bound components. PTAG's are also envisaged wherein X is selected such that it is capable of binding proteins, peptides, nucleic acid molecules, lipids, carbohydrates, steroids and the like.

Selective phosphorylation of diols with a Lewis acid catalyst

We report a method for the Lewis acid catalyzed phosphorylation of diols with pyrophosphates. Titanium alkoxides were found to be effective catalysts in the selective mono-phosphorylation for a range of diols. Diols 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-phosphorylated in up to 97% isolated yield. This structural core is mono-phosphorylated in numerous immunomodulating compounds including the FDA-approved drug, FTY720.

Direct mono-phosphorylation of 1,3-diols. A synthesis of FTY720-phosphate

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

Phosphonooxy and carbonate derivatives of taxol

The present invention is directed to novel taxol derivatives useful as anti-tumor agents. Also provided by this invention is pharmaceutical formulations and methods of treating mammalian tumors with the compounds of this invention.