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
• Article Data: 11

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

Description

5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE, with the CAS number 17331-22-5, is a nucleoside that plays a crucial role in the synthesis of oligonucleotides. It is characterized by its white to yellow powder form and is particularly utilized in the creation of triazoleand tetrazole-bridged nucleic acids, which are essential components in various molecular biology and biotechnology applications.

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

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 958-09-8 2'-deoxy-D-adenosine 
• 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 
• 84780-16-5 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine 
• 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 
• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 64911-19-9 9-((2R,4S,5R)-4-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamine 
• 289712-61-4 2-azidomethyl-N-[9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 
• 84765-88-8 2'-deoxy-N⁶-phthaloyladenosine 

Downstream Products

• 112677-85-7 Phosphoric acid diallyl ester (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 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 
• 89947-86-4 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 958-09-8 2'-deoxy-D-adenosine 
• 140613-55-4 2-cyanoethyl 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 3'-(N,N-diisopropyl)phosphoramidite 
• 89947-88-6 5'-O-N⁶-di-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 219649-87-3 C₄₉H₆₀N₉O₁₁PSi 
• 89947-92-2 Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-purin-9-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine 
• 89947-87-5 3'-O-t-butyldimethylsilyl-N,5'-O-bis(di-p-methoxytrityl) deoxyadenosine 
• 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

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

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.