81265-93-2

Basic information

• Product Name: 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine
• Synonyms: 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine;N6-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-adenosine;5'-DMT-2'-TBDMS-Bz-rA;N-(9-((2R,3R,4R,5R)-5-((Bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-3-((tert-butyldiMethylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzaMide;2'-O-t-ButyldiMethylsilyl-5'-O-(4,4'-diMethoxytrityl)-N6-benzoyl adenosine;N-benzoyl-5'-O-[bis(4-Methoxyphenyl)phenylMethyl]-2'-O-[(1,1-diMethylethyl)diMethylsilyl]-Adenosine;N-(9-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-but ldimethylsilyl)o;N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine
• CAS NO: 81265-93-2
• Molecular Formula: C₄₄H₄₉N₅O₇Si
• Molecular Weight: 787.97466
• EINECS: 2017-001-1
• Mol File: 81265-93-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 7.87±0.43(Predicted)
• CAS DataBase Reference: 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine(81265-93-2)
• EPA Substance Registry System: 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine(81265-93-2)

Safety Data

• Hazardous Substances Data: 81265-93-2(Hazardous Substances Data)

Usage

Description

5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine is a fluorescent adenosine-containing compound that is commonly used for the modification of DNA and RNA. It is characterized by the presence of a 5'-O-dimethoxytrityl (DMT) group, a 2'-O-tert-butyldimethylsilyl (TBDMS) group, and a benzoyl (Bz) group attached to the nitrogen atom. These modifications enhance the compound's stability and reactivity, making it a valuable tool in the field of molecular biology and biotechnology.

Uses

Used in Molecular Biology Research:
5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine is used as a fluorescent label for DNA and RNA molecules, allowing for the detection and analysis of these nucleic acids in various experimental setups. Its fluorescent properties enable researchers to monitor the hybridization, folding, and interactions of nucleic acids with other molecules, providing valuable insights into their structure and function.
Used in Synthetic Oligonucleotide Synthesis:
In the synthesis of synthetic oligonucleotides, 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine serves as a building block for the assembly of custom-designed sequences. The presence of the DMT group at the 5' end facilitates the coupling of the compound to other nucleotides during the solid-phase synthesis process, while the TBDMS group at the 2' position protects the hydroxyl group from unwanted reactions. The benzoyl group on the nitrogen atom further enhances the stability of the compound during synthesis.
Used in Diagnostic Applications:
5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine is also employed in the development of diagnostic assays and tests, where its fluorescent properties can be harnessed to detect specific DNA or RNA sequences associated with diseases or conditions. By incorporating this compound into probes or primers, researchers can design highly sensitive and specific diagnostic tools for various applications, including infectious disease detection, genetic testing, and environmental monitoring.
Used in Drug Discovery and Development:
The unique properties of 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine make it a valuable tool in the field of drug discovery and development. Its ability to interact with nucleic acids can be exploited to design molecules that target specific genes or regulatory elements, potentially leading to the development of new therapeutic agents for a wide range of diseases. Additionally, its fluorescent properties can be used to monitor the binding and activity of these molecules in cellular and animal models, aiding in the optimization of their efficacy and safety.

Upstream product

• 212375-93-4 3’,5’-O-bis(t-butylsilyl)-2’-O-(t-butyldimethylsilyl)adenosine 
• 401812-98-4 3’,5’-O-bis(t-butylsilyl)-2’-O-(t-butyldimethylsilyl)-N6-benzoyladenosine 
• 129666-75-7 6-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)adenosine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 4546-55-8 N-benzoyladenosine 
• 1348775-39-2 adenosine 
• 98-88-4 benzoyl chloride 
• 58-61-7 adenosine 
• 97219-09-5 3',5'-O-(Di-tert-butylsilanediyl)adenosine 
• 69504-07-0 N⁶-benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine 

Downstream Products

• 160056-44-0 C₁₀H₁₃N₅O₄SiC₆H₁₄PO₃HC(C₆H₅)3C₂H₃O₂C₇H₄C₆H₄ 
• 1005482-73-4 (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl trifluoromethane-sulfonate 
• 127553-42-8 5'-O-DMTr-2'-O-TBDMS-N-Bz-adenosine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 
• 75074-02-1 N⁶-Benzoyl-2'-O-(tert-butyldimethylsilyl)adenosin-3'-(o-chlorphenyl)(β-cyanethyl)phosphat 
• 170871-87-1 N-(9-((2R,3S,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 1374755-65-3 C₅₇H₆₅N₆O₈PS₂Si 
• 1222078-42-3 C₅₂H₅₄N₈O₈Si 

Relevant articles and documents

CYCLIC DINUCLEOTIDE COMPOUND AND USES THEREOF

Provided are a compound of formula (I), an optical isomer thereof, a pharmaceutically acceptable salt thereof, uses of said compound acting as a STING agonist.

CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE

Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.

Synthesis of 2'-O-substituted ribonucleosides.

An efficient synthesis of 2'-O-substituted ribonucleosides, including 2'-O-TBDMS and 2'-O-TOM protected as well as 2'-O-Me and 2'-O-allyl derivatives is presented. Di-t-butylsilylene group was employed for simultaneous protection of 3'- and 5'- hydroxyl functions of nucleoside on the first step. Subsequent silylation or alkylation of free 2'-OH followed by introduction of suitable protection on the base moiety and removal of cyclic silyl protection gave target compounds in a high yield.