98796-53-3

Usage

Uses

Used in Pharmaceutical Industry:
5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used as a key intermediate in the synthesis of antisense oligonucleotides for the development of novel therapeutic agents. These modified oligonucleotides, containing conformationally constrained methoxyaminomethylene, aminooxymethylene, and aminomethylene bridged nucleoside analogs, exhibit enhanced stability, binding affinity, and biological activity, making them promising candidates for the treatment of various diseases, including genetic disorders, viral infections, and cancer.
Used in Diagnostic Industry:
In the diagnostic field, 5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is employed in the development of highly sensitive and specific molecular probes for detecting and monitoring various diseases. The incorporation of these modified nucleoside analogs into the probes allows for improved hybridization properties, increased resistance to degradation, and enhanced signal-to-noise ratios, leading to more accurate and reliable diagnostic results.
Used in Research and Development:
5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is also utilized in academic and industrial research settings for the investigation of novel nucleic acid chemistry, structure-function relationships, and the development of new methodologies for the synthesis and modification of oligonucleotides. 5'-O-(4,4'-Dimethoxytrityl)-N6-benzoyl-2'-deoxyadenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite serves as a valuable tool for advancing our understanding of nucleic acid biology and the design of innovative therapeutic and diagnostic agents.

Physical form

Powder or granules

Color

White to off-white

InChI:InChI=1/C21H23NO3.C8H11NO2.C3H6N2O2P/c23-20(25-19-15-22-13-11-16(19)12-14-22)21(24,17-7-3-1-4-8-17)18-9-5-2-6-10-18;9-4-3-6-1-2-7(10)8(11)5-6;1-3(2-4)7-8(5)6/h1-10,16,19,24H,11-15H2;1-2,5,10-11H,3-4,9H2;3H,5H2,1H3/q;;-1

Upstream product

• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 174647-46-2 2-cyanoethoxy(N,N-diisopropylamino)3-nitro-1,2,4-triazolylphosphine 
• 131420-63-8 2-O-cyanoethyl-N,N,N’,N’-tetraisopropylphosphordiamidite 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 133728-84-4 C₅₀H₆₂N₇O₆P 
• 109-78-4 3-Hydroxypropionitrile 
• 108-18-9 diisopropylamine 
• 17425-88-6 N,N-diisopropyl-1,1,1-trimethylsilylamine 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 

Downstream Products

• 119484-01-4 O-2-cyanoethyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate 
• 23339-47-1 d(ApT) 
• 118380-95-3 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-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 
• 863507-31-7 C₅₆H₅₇N₈O₁₄PS 
• 262429-99-2 4-oxo-pentanoic acid 5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[{5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-cyano-ethoxy)-thiophosphoryloxymethyl]-tetrahydro-furan-3-yl ester 
• 725223-47-2 C₄₇H₅₂N₇O₇P 
• 863507-25-9 5'-OH-dA^Bzps_CNEdT-3'-O-Lev 
• 224186-71-4 4-oxo-pentanoic acid 2-[{5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-(2-cyano-ethoxy)-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 140613-55-4 2-cyanoethyl 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 3'-(N,N-diisopropyl)phosphoramidite 

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.

BICYCLIC PEPTIDE LIGAND STING CONJUGATES AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Microwave-assisted preparation of nucleoside-phosphoramidites

Microwave-assisted phosphitylation of sterically hindered nucleosides is demonstrated to be an efficient method for the preparation of corresponding phosphoramidites (otherwise onerous under standard conditions) and is shown to be general in its applicability. the Partner Organisations 2014.

Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry

Ionic liquids have been used in combination with ball milling on a range of chlorophosphoramidite reagents to phosphitylate nucleosides and 2-deoxynucleosides. The enhanced stability offered by the ionic liquid mediated processes combined with efficient mass transfer induced by ball milling has enabled excellent yields to be obtained even when using small dialkyl amino groups as well as the more commonly used diisopropylamino protection.

Selective synthesis of chlorophosphoramidites using ionic liquids

A range of chlorophosphoramidites have been prepared in ionic liquids and compared with material synthesised in molecular solvents. Through the use of ionic liquids as reaction media the moisture sensitivity and impurity issues hampering existing traditio

PROCESS FOR PRODUCING PHOSPHOROAMIDITE

The present invention provides high purity phosphoroamidite products by reducing the amount of impurities of triphosphite which has been additionally produced according to the conventional technique.Phosphoroamidites can be obtained with high purity such that the excess reaction is suppressed by using a reaction activator hardly generating triphosphite.According to the present invention, phosphoroamides can be obtained with high purity, which has heretofore been difficult to suppress the generation of impurities of triphosphite.

PHOSPHITYLATION PROCESS

A process for the phosphitylation of an alcohol or thiol with a phosphitylation agent in the presence of an activator is provided. The activator has the formula (1): wherein p is 0 or an integer from 1 to 4 and R for each occurrence is a substituent. Pref

Methods of producing phosphitylated compounds

Provided are methods of producing phosphitylated compounds, including 3′-O-phosphoramidites, comprising the step of reacting a hydroxyl-containing compound with a phosphitylating agent in the presence of a phosphitylation activator selected from the group consisting of: (1) acid-base complexes derived from an amine base of Formula I 1wherein R, R1, and R2 are independently C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl; (2) acid-base complexes derived from an amine base of Formula II 2wherein R3, R4, R5, R6, and R7 are independently hydrogen, C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl, and at least one of R3, R4, R5 R6, and R7 is not hydrogen.; (3) acid-base complexes derived from a diazabicyclo amine base; (4) zwitterionic amine complexes; and (5) combinations of two or more thereof, to produce a phosphitylated compound.

Method of preparing phosphoramidites

Improved methods for preparation of phosphoramidite compounds are disclosed. The phosphoramidites are useful, for example, for the preparation of oligonucleotides by solid state oligonucleotide synthetic regimes.

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.