98796-51-1

Basic information

• Product Name: 5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
• Synonyms: 5'-O-DMT-thymidine 3'-CE phosphoramidite;DMT-dT PhosphoraMidite;5'-O-[Bis(4-Methoxyphenyl)phenylMethyl]-thyMidine 3'-[2-cyanoethyl N,N-bis(1-Methylethyl)phosphoraMidite];5′-O-(4,4′-dimethoxytrityl)-2′-deoxythymidine-3′-O-[O-(2-cyanoethyl)-N,N′-diisopropylphosphoramidite];5'-O-DMT-2'-deoxythymidine-3'-CE Phosphoramidite;5'-O-(4,4'-Dimethoxytrityl)-2'-deoxy-5-methyluridine-3'-O-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite;5'-O-(4,4'-Dimethoxytrityl)-thymidine-3'-cyanoethyl Phosphoramidite;5'-O-DMT- 2'-Deoxy Thymidine Phosphoramidite
• CAS NO: 98796-51-1
• Molecular Formula: C₄₀H₄₉N₄O₈P
• Molecular Weight: 744.81
• EINECS: 2017-001-1
• Mol File: 98796-51-1.mol
• Article Data: 23

Chemical Properties

• Appearance: white to off-white/
• Density: 1.22 at 20℃
• Vapor Pressure: 0-0Pa at 20-50℃
• Storage Temp.: Store at -20°C
• Solubility: soluble, clear
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite(98796-51-1)
• EPA Substance Registry System: 5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite(98796-51-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 98796-51-1(Hazardous Substances Data)

Usage

Description

5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite is a nucleotide and reactant that plays a crucial role in the synthesis of various types of oligonucleotides. It is characterized by its ability to facilitate the formation of phosphorothioate linkages and the creation of lipophilic 5'-phosphoramidate derivatives, which are essential for the development of novel therapeutic agents and diagnostic tools in molecular biology and medicine.

Uses

Used in Pharmaceutical Industry:
5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite is used as a key reactant in the solid-phase synthesis of phosphorothioate oligonucleotides. These modified oligonucleotides exhibit increased stability and resistance to nuclease degradation, making them suitable for applications such as antisense therapy, where they can modulate gene expression and target specific RNA sequences to treat various diseases.
Used in Diagnostics and Research:
In the field of diagnostics and research, 5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite is utilized for the synthesis of lipophilic 5'-phosphoramidate derivatives of DNA and RNA oligonucleotides. These derivatives possess enhanced cellular uptake and membrane permeability, allowing for improved delivery of oligonucleotides into cells for applications such as in situ hybridization, molecular beacons, and other detection techniques.
Used in Drug Development:
5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite is also employed in the development of novel therapeutic agents, such as antiviral and anti-cancer drugs. The ability to create stable and lipophilic derivatives of oligonucleotides enables the design of drugs that can effectively target specific genetic sequences and disrupt disease-causing processes.
Overall, 5'-Dimethoxytrityl-3'-deoxythymidine 2'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite is a versatile and essential component in the synthesis of various types of oligonucleotides, with applications spanning across the pharmaceutical, diagnostic, and research industries. Its unique properties and reactivity make it a valuable tool for the development of innovative therapeutic agents and diagnostic techniques.

InChI:InChI=1/C10H14N2O5.C3H6N2O2P/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8;1-3(2-4)7-8(5)6/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16);3H,5H2,1H3/q;-1/t6-,7+,8+;/m0./s1

Upstream product

• 148134-86-5 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 17425-88-6 N,N-diisopropyl-1,1,1-trimethylsilylamine 
• 108-18-9 diisopropylamine 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 50-89-5 thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 174647-46-2 2-cyanoethoxy(N,N-diisopropylamino)3-nitro-1,2,4-triazolylphosphine 
• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 109-78-4 3-Hydroxypropionitrile 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 

Downstream Products

• 813419-53-3 Phosphorous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2-cyano-ethyl) ester 
• 4719-57-7 TpTpTpTp 
• 169049-63-2 2-Cyanoethyl 5'-O-(dimethoxytrityl)thymidin-3'-yl N-(phenylacetyl)phosphoramidate 
• 224298-18-4 5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-β-cyanoethyl phosphorothioate 
• 102987-83-7 5′-O-(4,4′-dimethoxytrityl)thymidine-3′-O-[2-cyanoethyl]phosphonate 
• 187539-25-9 C₄₉H₅₄N₅O₁₅PS 
• 224186-67-8 5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinyl dithymidyl 2-cyanoethyl phosphate 
• 725223-48-3 C₄₀H₄₉N₄O₈P 

Relevant articles and documents

Resolved P-metalated nucleoside phosphoramidites

The synthesis of resolved P-metalated nucleoside phosphoramidites is described. These rare compounds were initially prepared with gold as the metal center; however, the gold can be removed using basic phosphines or solid-supported triphenylphosphine. Treatment of the free nucleoside phosphoramidite with a platinum source generated a unique platinated dinucleoside species with a diastereomeric ratio of >99:1.

Oxidative substitution of boranephosphonate diesters as a route to post-synthetically modified DNA

The introduction of modifications into oligonucleotides is important for a large number of applications in the nucleic acids field. However, the method of solid-phase DNA synthesis presents significant challenges for incorporating many useful modifications that are unstable to the conditions for preparing synthetic DNA. Here we report that boranephosphonate diesters undergo facile nucleophilic substitution in a stereospecific manner upon activation by iodine. We have subsequently used this reactivity to post-synthetically introduce modifications including azides and fluorophores into DNA by first synthesizing boranephosphonate-linked 2′-deoxyoligonucleotides and then treating these oligomers with iodine and various nucleophiles. In addition, we show that this reaction is an attractive method for preparing stereodefined phosphorus-modified oligonucleotides. We have also examined the mechanism of this reaction and show that it proceeds via an iodophosphate intermediate. Beyond nucleic acids synthesis, due to the ubiquity of phosphate derivatives in natural compounds and therapeutics, this stereospecific reaction has many potential applications in organophosphorus chemistry.

Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA

Two types of neamine derivatives, neamine-dinucleotide conjugates 8a-g and neamine-PNA conjugates 12a-c and 14a-d, were synthesized. Compound 8a-g were synthesized by the condensation of azido-neamine with dinucleotide-5′-carboxylic acids, followed by reduction and deprotection. Compound 12a-c and 14a-d were synthesized by the similar strategy. The binding affinities of conjugates 8a-g, 12a-c, and 14a-d towards 16S RNA, 18S RNA, and TAR RNA were evaluated by SPR. It indicates that conjugates 12a-c and 14a-d interact with 16S, 18S RNA at the same level as that of neamine, 14a and 14d show about twofold binding affinities to TAR RNA compared to that of neamine. However, the neamine-dinucleotide conjugates 8a-g exhibit very weak binding affinities to 16S, 18S, and TAR RNA, computer modelling results that negative-negative electrostatic repulsion of phosphate group in compound 8a-g and RNA leads to a sharp decrease of the binding affinities compared with that of neamine, neamine-nucleoside and neamine-PNA conjugates.