17331-22-5

Basic information

• Product Name: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE
• Synonyms: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine≥ 97% (HPLC);DMT-DA;5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE;5'-O-(4 4'-DIMETHOXYTRITYL)-2'- &;Adenosine, 5'-O-[bis(4-Methoxyphenyl)phenylMethyl]-2'-deoxy-
• CAS NO: 17331-22-5
• Molecular Formula: C₃₁H₃₁N₅O₅
• Molecular Weight: 553.61
• Mol File: 17331-22-5.mol

Chemical Properties

• Melting Point: 97-98 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• Boiling Point: 785.1±70.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 13.75±0.60(Predicted)
• CAS DataBase Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE(17331-22-5)
• EPA Substance Registry System: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE(17331-22-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17331-22-5(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology and Biotechnology Applications:
5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE is used as a key component in the synthesis of oligonucleotides for the development of triazoleand tetrazole-bridged nucleic acids. These bridged nucleic acids are vital for enhancing the stability and specificity of nucleic acid duplexes, which are essential in various molecular biology techniques and biotechnological applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE is used as a building block for the development of novel therapeutic agents targeting various diseases. Its role in the synthesis of oligonucleotides allows for the creation of specific drug candidates that can potentially modulate gene expression or interfere with disease-causing genetic elements.
Used in Research and Development:
5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE is also utilized in research and development settings, where it serves as a valuable tool for studying the structure, function, and interactions of nucleic acids. Its application in the synthesis of bridged nucleic acids can provide insights into the underlying mechanisms of genetic regulation and contribute to the advancement of gene therapy and other molecular medicine approaches.

Upstream product

• 84765-88-8 2'-deoxy-N⁶-phthaloyladenosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 958-09-8 2'-deoxy-D-adenosine 
• 289712-61-4 2-azidomethyl-N-[9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 
• 64911-19-9 9-((2R,4S,5R)-4-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamine 
• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 329781-61-5 2-azidomethyl-N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide 
• 84780-16-5 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine 
• 187674-19-7 (9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester 

Downstream Products

• 134817-00-8 Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester methyl ester 
• 89947-88-6 5'-O-N⁶-di-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 1186079-74-2 C₃₈H₃₇N₆O₉P 
• 51549-31-6 3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 102064-50-6 5'-O-(4,4'-dimethoxytrityl)-3'-O-succinyl-2'-deoxyadenosine 
• 1234342-09-6 5'-O-DMTr-2'-deoxyadenosine 3'-O-oxazaphospholidine 
• 170236-42-7 C₄₅H₃₉N₅O₇ 
• 1133959-35-9 C₄₄H₅₀N₈O₅Si 
• 125138-92-3 N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite) 
• 125172-13-6 {9-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-carbamic acid allyl ester 
• 108554-88-7 N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 
• 100649-06-7 C₅₀H₅₁ClN₇O₁₄P 
• 100649-08-9 C₄₇H₄₇ClN₇O₁₂P 
• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 

Relevant articles and documents

Transient Protection: Efficient One-Flask Syntheses of Protected Deoxynucleosides

Application of the concept of transient protection to the synthesis of protected deoxynucleosides is described.The deoxynucleosides are first treated with trimethylchlorosilane in pyridine for protection of the hydroxyl groups, and then immediately reacted with an acylating agent - benzoyl chloride for 1a and 1b and isobutyric anhydride for 1c - to effect N-acylation.Hydrolysis of the trimethylsilyl groups takes a few hours in aqueous pyridine or a few minutes with dilute ammonia.The ammonia also effects selective hydrolysis of the initially formed N,N-dibenzoyldeoxyadenosine derivative (3a) to the desired N-benzoyldeoxyadenosine (4a).This one-flask procedure gives crystalline N-acyl deoxynucleosides 4a and 4b in 95percent yield and 4c in 75percent yield, in only a few hours.The 5'-O-dimethoxytrityl deoxynucleosides 8a and 8b are also obtained in a one-flask procedure by initial reaction of the deoxynucleosides with 4,4'-dimethoxytrityl chloride, followed by treatment with trimethylchlorosilane and then benzoyl chloride.Although with deoxycytidine some of the 4-N,5'-O-bis(dimethoxytrityl) derivative (5c) is formed, benzoyl chloride effects conversion to the 4-N-benzoyl derivative (7b).After simple purification by flash chromatography 8a and 8b are each obtained in 80-90percent overall yield from 1a or 1b.

Characterization of high molecular weight impurities in synthetic phosphorothioate oligonucleotides

Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using 2′-deoxyadenosine- or 2′-O-(2-methoxyethyl)-5- methylcytosine-loaded solid supports contain branched impurities consisting of two chains linked through the exocycl

MODIFIED NUCLEOTIDES FOR SYNTHESIS OF NUCLEIC ACIDS, A KIT CONTAINING SUCH NUCLEOTIDES AND THEIR USE FOR THE PRODUCTION OF SYNTHETIC NUCLEIC ACID SEQUENCES OR GENES

A modified nucleotide, intended for the synthesis of long chain nucleic acids by enzymatic processes, comprising a “natural” nitrogenous base or a natural nitrogenous base analogue, a ribose or deoxyribose carbohydrate, and at least one phosphate group, characterized in that said nucleotide comprises at least one R group, termed the modifier group, carried by said nitrogenous base or analogue and/or by the oxygen in position 3′ of the ribose or deoxyribose molecule, making it possible to block the polymerization of said nucleotide and/or to allow the interaction of said nucleotide with another molecule, such as a protein, during the nucleic acid synthesis, R comprising at least one functional terminal group.

Conversion of adenine to 5-amino-4-pyrimidinylimidazole caused by acetyl capping during solid phase oligonucleotide synthesis

The acetyl capping reaction used throughout solid phase oligonucleotide synthesis is meant to minimize n?1 deletionmer impurities by terminating sequences that fail to couple to a phosphoramidite. However, the reaction is also responsible for the formatio

Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors

Disaccharide nucleosides constitute an important group of naturally-occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O-glycosylation of nucleoside acceptors, such as adenosine, guanosine, thy

2-(Azidomethyl)benzoyl as a new protecting group in nucleosides

A new protecting group, 2-(azidomethyl)benzoyl (AZMB), which can be easily removed by treatment with MePPh2 in dioxane-H2O or reduction with HCOONH4-Pd/C in dioxane-MeOH, was developed for protection of the hydroxy and amino functions of deoxyribonucleosides.

Nucleotides: Part LXI: Phthaloyl strategy: A new concept of oligonucleotide synthesis

A new alternative strategy of oligonucleotide synthesis was developed by use of the phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9-12). This approach combines the advantages of cheap and easily accessible monomeric building blocks (see 17- 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

Nucleotides. Part L. Aglycone protection by the (2-dansylethoxy)carbonyl (= {2-{5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group - A new variation in oligodeoxyribonucleoside synthesis

The (2-dansylethoxy)carbonyl (= {2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group was employed for protection of the amino functions of the aglycone residues. The lactam function of 2'-deoxyguanosine was on the one hand unprotected and on the other hand alkylated at O6 of the aglycone with the 2-(4-nitrophenyl)ethyl (npe) and 2-(phenylsulfonyl)ethyl (pse) group, respectively. The syntheses of monomeric building blocks, both phosphoramidites and nucleoside-functionalized supports, are described for the three common 2'-deoxynucleosides (2'-deoxycytidine, 2'-deoxyadenosine, 2'-deoxyguanosine). As kinetic studies with the tritylated nucleosides showed, the dnseoc group is more labile towards DBU cleavage than the corresponding 2-(4-nitrophenyl)ethyl-(npe) and [2-(4-nitrophenyl)ethoxy]carbonyl(npeoc)-protected analogues. These results were confirmed by the very fast deprotection rate of the dnseoc groups at some oligonucleotides.

The allylic protection method in solid-phase oligonucleotide synthesis. An efficient preparation of solid-anchored DNA oligomers

The first efficient synthesis of solid-anchored DNA oligomers has been realized; it relies on the use of allyl and (allyloxy)carbonyl groups as protectors of internucleotide linkage and nucleoside bases, respectively, in conjunction with palladium chemist

STEREOSPECIFIC SYNTHESIS OF DINUCLEOSIDE MONOPHOSPHATE ARYL ESTERS BY USING NEW CONDENSING REAGENTS

New condensing reagents, arenesulfonyl 5-(pyridin-2-yl)tetrazoles have been synthesized and used for stereospecific synthesis of dinucleoside monophosphate aryl esters.