220592-63-2

Basic information

• Product Name: phenyl (tert-butyloxy-L-alaninyl)phosphorochloridate
• Synonyms: phenyl (tert-butyloxy-L-alaninyl)phosphorochloridate
• CAS NO: 220592-63-2
• Molecular Weight: 319.725
• Mol File: 220592-63-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: phenyl (tert-butyloxy-L-alaninyl)phosphorochloridate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl (tert-butyloxy-L-alaninyl)phosphorochloridate(220592-63-2)
• EPA Substance Registry System: phenyl (tert-butyloxy-L-alaninyl)phosphorochloridate(220592-63-2)

Safety Data

• Hazardous Substances Data: 220592-63-2(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 770-12-7 O-phenyl phosphorodichloridate 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 

Downstream Products

• 1170666-23-5 C₂₈H₃₅N₈O₉P 

Relevant articles and documents

Generation of Stable Isopentenyl Monophosphate Aryloxy Triester Phosphoramidates as Activators of Vγ9Vδ2 T Cells

Aryloxy triester phosphoramidate prodrugs of the monophosphate derivatives of isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) were synthesized as lipophilic derivatives that can improve cell uptake. Despite the structural similarity of IPP and DMAPP, it was noted that their phosphoramidate prodrugs exhibited distinct stability profiles in aqueous environments, which we show is due to the position of the allyl bond in the backbones of the IPP and DMAPP monophosphates. As the IPP monophosphate aryloxy triester phosphoramidates showed favorable stability, they were subsequently investigated for their ability to activate Vγ9/Vδ2 T cells and they showed promising activation of this subset of T cells. Together, these findings represent the first report of IPP and DMAPP monophosphate prodrugs and the ability of IPP aryloxy triester phosphoramidate prodrugs to activate Vγ9/Vδ2 T cells highlighting their potential as possible immunotherapeutics.

Kinetin Riboside and Its ProTides Activate the Parkinson’s Disease Associated PTEN-Induced Putative Kinase 1 (PINK1) Independent of Mitochondrial Depolarization

Since loss of function mutations of PINK1 lead to early onset Parkinson’s disease, there has been growing interest in the discovery of small molecules that amplify the kinase activity of PINK1. We herein report the design, synthesis, serum stability, and hydrolysis of four kinetin riboside ProTides. These ProTides, along with kinetin riboside, activated PINK1 in cells independent of mitochondrial depolarization. This highlights the potential of modified nucleosides and their phosphate prodrugs as treatments for neurodegenerative diseases.

Antiviral phosphoramidates

The invention provides novel nucleoside compounds of formula I wherein R1, R2a, R2b, R3, R4, R5, R6, R8a, R9 and R10 are as defined herein which are useful for the treatment of Hepatitis C Virus (HCV) mediated diseases. The invention further provides methods for treatment or prophylaxis of HCV mediated diseases with compounds of formula I and pharmaceutical compositions comprising these compounds,