110764-79-9

Usage

Uses

Used in Organic Synthesis:
5'-O-(4,4-Dimethoxytrityl)-2'-O-methyluridine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used as a reagent for the synthesis of modified RNA sequences, providing a protective function through its DMT group to ensure the integrity of the RNA during the synthesis process.
Used in Genetic Testing and Research:
In the field of genetic testing and research, 5'-O-(4,4-Dimethoxytrityl)-2'-O-methyluridine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used as a component in the creation of oligonucleotides, which are essential for probing genetic material and understanding gene function.
Used in Forensic Science:
5'-O-(4,4-Dimethoxytrityl)-2'-O-methyluridine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used as a key component in the synthesis of oligonucleotides for forensic applications, where precise identification and analysis of genetic material are crucial for solving crimes and legal proceedings.
Used in Therapeutic Applications:
In therapeutic applications, 5'-O-(4,4-Dimethoxytrityl)-2'-O-methyluridine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used in the development of modified RNA molecules that can be employed for targeted therapies, such as RNA interference or antisense therapies, to treat various diseases by modulating gene expression at the RNA level.
Used in Pharmaceutical Industry:
5'-O-(4,4-Dimethoxytrityl)-2'-O-methyluridine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used as a building block in the pharmaceutical industry for the synthesis of novel RNA-based drugs, which have the potential to treat a wide range of diseases by modulating gene expression and protein synthesis.

Upstream product

• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 103285-22-9 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine 

Relevant academic research and scientific papers

ON-DEMAND PHOSPHORAMIDITE SYNTHESIS

The invention relates to a method of synthesis of phosphoramidites by immobilization of a phosphitylation agent on a resin activated to create a charged resin, then putting in contact with the charged resin with a suitable substrate. Phosphoramidites are synthesized in a few minutes from the application of the starting materials. Thus, the process makes it possible to create specific phosphoramidites on demand when they are needed in other applications. The substrates to be applied are mainly nucleosides, thus making it possible to create nucleoside phosphoramidites for the subsequent synthesis of oligonucleotides.

Improved process for the preparation of nucleosidic phosphoramidites using a safer and cheaper activator

A new, simplified commercial process for the preparation of nucleosidic phosphoramidites, key raw materials for the automated solid-supported synthesis of oligonucleotide-based drugs, was developed. Phosphitylation of a variety of protected nucleosidic derivatives (1-4) with a small excess of 2-cyanoethyl-N,N,N′,N′-tetraisopropyl phosphoramidite (5, bis-reagent) and pyridinium trifluoroacetate (Py·TFA) as the activator in an appropriate solvent at room temperature formed 75-96% of desired nucleosidic phosphoramidite products in less than 2 h. An efficient nonaqueous work-up has been developed to further streamline the isolation of moisture-sensitive P(III) nucleosidic compounds. The key finding is the use of Py·TFA, which is effective, inexpensive, stable, less acidic (pKa 5.2) than 1H-tetrazole, nontoxic, safe, and highly soluble in organic solvents. The reaction mechanism for phosphitylation with Py TFA as an activator has also been studied. An improved, robust, and versatile process for the preparation of nucleotide phosphoramidites under very concentrated reaction conditions was developed to support commercial manufacture of oligonucleotide-based drugs.

Process for the preparation of 2'-O-alkyl purine phosphoramidites

2'-O-alkylated guanosine, uridine, cytidine, and 2,6-diaminopurine 3'-O-phosphoramidites are prepared by alkylating nucleoside precursors, adding suitable blocking groups and phosphitylating. Alkylation is effected on 2,6-diamino-9-(β-D-ribofuranosyl)purine followed by deamination to prepare guanosine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected on a dialkyl stannylene derivative of uridine to prepare uridine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected directly on cytidine to prepare cytidine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected directly on 2,6-diaminopurine to prepare 2,6-diaminopurine 2'-O-alkylated 3'-O-phosphormidites.