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

Uses

5''-O-[Bis(4-Methoxyphenyl)phenylmethyl]-thymidine 3''-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite] is a nucleotide and reactant used in the solid-phase synthesis of phosphorothioate oligonucleotides, and in the synthesis of lipophilic 5''-phosphoramidate derivatives of DNA and RNA oligonucleotides.

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

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

Downstream Products

• 187539-25-9 C₄₉H₅₄N₅O₁₅PS 
• 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 
• 830322-65-1 5'-(dimethoxytrityl)-2'-deoxythymidine-3'-(1-dodecyl)ammonium phosphate 
• 1208070-45-4 C₄₁H₄₆N₃O₁₁P 
• 1397776-01-0 C₃₂H₄₅N₄O₁₂PSSi 
• 1397776-03-2 C₂₆H₃₁N₄O₁₂PS 
• 1443257-89-3 C₂₆H₃₁N₄O₁₃PS 
• 1969-54-6 thymidylyl (3',5')thymidine 

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.