110782-31-5

Basic information

• Product Name: 2’-O-Methyl-rA(N-Bz)phosphoramidite
• Synonyms: 2’-O-Methyl-rA(N-Bz)phosphoramidite;N-blocked-5'-O-DMT-2'-O-Me CED adenosine phosphoramidite;5'-O-DMT-2'-O-Me-rA(N-Bz)-3'-CEDPA;N-Benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methyladenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite;2'-OMe-Bz-A Phosphoramidite;Ac-dA Phosphoramidite;5'-O-DMT-2'-O-Me-A(bz) phosphoramidite;2'OMe-A CE PhosphoraMidite
• CAS NO: 110782-31-5
• Molecular Formula: C₄₈H₅₄N₇O₈P
• Molecular Weight: 887.97
• EINECS: 200-100-5
• Mol File: 110782-31-5.mol
• Article Data: 2

Chemical Properties

• Appearance: white to off-white/
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 7.87±0.43(Predicted)
• CAS DataBase Reference: 2’-O-Methyl-rA(N-Bz)phosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: 2’-O-Methyl-rA(N-Bz)phosphoramidite(110782-31-5)
• EPA Substance Registry System: 2’-O-Methyl-rA(N-Bz)phosphoramidite(110782-31-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 110782-31-5(Hazardous Substances Data)

Usage

Description

2’-O-Methyl-rA(N-Bz)phosphoramidite, also known as (2R,3R,4R,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-methoxytetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite, is a nucleotide characterized by its white or off-white powder form. It plays a crucial role in the synthesis of native-like crosslinked duplex RNA, which has potential applications in various fields.

Uses

Used in RNA Synthesis:
2’-O-Methyl-rA(N-Bz)phosphoramidite is used as a nucleotide building block for the synthesis of native-like crosslinked duplex RNA. Its incorporation into RNA structures allows for the creation of more stable and functional RNA molecules, which can be utilized in various applications.
Used in Biomedical Research:
In the field of biomedical research, 2’-O-Methyl-rA(N-Bz)phosphoramidite is used as a key component in the development of RNA-based therapeutics and diagnostic tools. Its ability to enhance the stability and functionality of RNA molecules makes it a valuable asset in the design of novel RNA drugs and probes for detecting specific genetic sequences.
Used in Nanotechnology:
2’-O-Methyl-rA(N-Bz)phosphoramidite also finds application in nanotechnology, where it can be used to create self-assembled RNA structures with specific functions. These structures can be employed in various applications, such as drug delivery systems, biosensors, and nanodevices, due to their unique properties and capabilities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2’-O-Methyl-rA(N-Bz)phosphoramidite is used as a starting material for the synthesis of modified nucleotides, which can be incorporated into RNA-based drugs. These modified nucleotides can improve the stability, specificity, and efficacy of RNA therapeutics, leading to the development of more effective treatments for various diseases.
Overall, 2’-O-Methyl-rA(N-Bz)phosphoramidite is a versatile nucleotide with a wide range of applications in various industries, including RNA synthesis, biomedical research, nanotechnology, and pharmaceuticals. Its unique properties and potential uses make it an important compound for the development of innovative solutions in these fields.

Upstream product

• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 110764-72-2 N⁶-benzoyl-5'-(4,4'-dimethoxytrityl)-O^2'-methyladenosine 

Downstream Products

• 1427269-35-9 N⁶-(benzoyl)-2'-O-methyladenosine 3'-(allyl 2-cyanoethyl phosphate) 
• 118362-06-4 Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester; compound with ammonia 

Relevant articles and documents

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.