1097131-05-9

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine
• Synonyms: 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine
• CAS NO: 1097131-05-9
• Molecular Weight: 817.896
• Mol File: 1097131-05-9.mol

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine(1097131-05-9)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine(1097131-05-9)

Safety Data

• Hazardous Substances Data: 1097131-05-9(Hazardous Substances Data)

Upstream product

• 53064-79-2 iodomethyl pivaloate 
• 121076-16-2 5'-O-dimethoxytrityl-N₆-phenoxyacetyladenosine 
• 18997-19-8 Chloromethyl pivalate 

Relevant articles and documents

Solid-phase synthesis of 5′-triphosphate 2′-5′- oligoadenylates analogs with 3′-O-biolabile groups and their evaluation as RNase L activators and antiviral drugs

5′-Triphosphate 2′-5′-oligoadenylate (2-5A) is the central player in the 2-5A system that is an innate immunity pathway in response to the presence of infectious agents. Intracellular endoribonuclease RNase L activated by 2-5A cleaves viral and cellular RNA resulting in apoptosis. The major limitations of 2-5A for therapeutic applications is the short biological half-life and poor cellular uptake. Modification of 2-5A with biolabile and lipophilic groups that facilitate its uptake, increase its in vivo stability and release the parent 2-5A drug in an intact form offer an alternative approach to therapeutic use of 2-5A. Here we have synthesized the trimeric and tetrameric 2-5A species bearing hydrophobic and enzymolabile pivaloyloxymethyl groups at 3′-positions and a triphosphate at the 5′-end. Both analogs were able to activate RNase L and the production of the trimer 2-5A (the most active) was scaled up to the milligram scale for antiviral evaluation in cells infected by influenza virus or respiratory syncytial virus. The trimer analog demonstrated some significant antiviral activity.

A base-labile group for 2′-OH protection of ribonucleosides: A major challenge for RNA synthesis

A base-labile group for 2'-OH protection of ribonucleosides was investigated. The solid support was dried by blowing argon through a DNA synthesizer and was first treated with 10% anhydrous piperidine in CH 3CN at room temperature for 15 minutes to eliminate cyanoethyl groups from phosphates. The piperidine solution was removed from the column and the solid support was washed with CH3CN. The three ammoniacal eluates were collected in a screw-capped glass vial and were left at room temperature for a further 1.5 hours to completely deprotect nucleobases and 2'-hydroxyl groups. The fully deprotected oligonucleotide was transferred to a 50 mL round-bottomed flask and isopropylamine was added to the solution before evaporation to dryness. It was observed that PivOM method provides highly pure RNA without any additional desalting step.