64325-78-6

Basic information

• Product Name: N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
• Synonyms: 5'-O-(4,4'-DIMETHOXYTRITYL)-N6-BENZOYL-2'-DEOXYADENOSINE;5'-O-DIMETHOXYTRITYL-N-BENZOYL DESOXYADENOSINE;5'-O-DMT-N6-BZ-2'-DEOXYADENOSINE;N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine;5'-O-Dimethylterephthalate-N-benzoyl-2-deoxyadenosine;N(6)-BENZOYL-5'-O-(4 4'-DIMETHOXYTRITYL&;N(6)-BENZOYL-5'-O-(4,4'-DIMETHOXY TRITYL) -2'-DEOXY ADENOSINE (DMT-DA-BZ);bz-dmt-da
• CAS NO: 64325-78-6
• Molecular Formula: C₃₈H₃₅N₅O₆
• Molecular Weight: 657.71
• EINECS: 264-776-4
• Product Categories: Organics;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents
• Mol File: 64325-78-6.mol

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 681.42°C (rough estimate)
• Appearance: WHITE TO WHITE WITH A YELLOW CAST POWDER
• Density: 1.2199 (rough estimate)
• Refractive Index: -10 ° (C=1, MeOH)
• Storage Temp.: −20°C
• PKA: 7.87±0.43(Predicted)
• Water Solubility: 140μg/L at 20℃
• CAS DataBase Reference: N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine(64325-78-6)
• EPA Substance Registry System: N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine(64325-78-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 1-3-10
• Hazardous Substances Data: 64325-78-6(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

Upstream product

• 119484-01-4 O-2-cyanoethyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 118352-75-3 Triethylammonium 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 3'-H-phosphonate 
• 226415-08-3 N-(9-((2R,3S,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 144924-99-2 N-(9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 98796-53-3 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] 
• 64723-02-0 N-benzoyl-3',5'-di-O-benzoyl-2'-deoxyadenosine 
• 958-09-8 2'-deoxy-D-adenosine 
• 17331-22-5 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine 
• 40615-35-8 4,4'-dimethoxytrityl alcohol 

Downstream Products

• 74405-42-8 Succinic acid mono-{(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl} ester 
• 25152-95-8 3'-O-acetyl-N-benzoyl-2'-deoxyadenosine 
• 93966-66-6 N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxyadenosine 3'-benzoate 
• 146578-12-3 5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine 
• 51549-40-7 6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 93134-36-2 5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3'-O-levulinoyl-2'-deoxyadenosine 
• 71100-59-9 C₄₄H₃₈ClN₅O₉P^(1-) 
• 82739-92-2 N⁶-Benzoyl-P-methyl-5'-O-dimethoxytrityl-2'-deoxyadenosyl-(3'5')-2'-deoxythymidine 
• 93134-54-4 Phosphoric acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester methyl ester 
• 119484-01-4 O-2-cyanoethyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate 
• 125272-41-5 C₄₆H₅₄N₇O₆P 
• 74212-29-6 Phosphoric acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 2,2,2-trichloro-ethyl ester 
• 64325-79-7 4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2'-deoxyadenosin-3'-yl phosphate 
• 84432-77-9 Diethyl-phosphoramidous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester methyl ester 

Relevant articles and documents

BICYCLIC PEPTIDE LIGAND STING CONJUGATES AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Tritylation of alcohols under mild conditions without using silver salts

Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was also tested on four nucleoside derivatives that have primary alcohols. Satisfactory results were also obtained.

Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides

An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.

Method for purifying 5'-protected 2'-deoxypurine nucleosides

A method for efficiently purifying 5' protected 2'-deoxypurine nucleosides, efficient production of which has previously been difficult. Impurities can be separated by obtaining the 5' protected 2'-deoxypurine nucleoside as an inclusion crystal including a solvent such as that having a nitrile structure in order to purify the 5' protected 2'-deoxypurine nucleoside at a high purity. This invention enables synthesis of highly purified protected deoxypurine nucleosides easily on a large scale, which has previously been performed by column chromatography method.

Nucleoside recovery in DNA and RNA synthesis

Nucleoside phosphoramidites and H-phosphonate diesters can be converted to nucleosides under mild conditions and in high yields by reaction with polyhydroxy alcohols.

A mild and efficient method for the preparation of 5'-dimethoxytrityl- 2'-deoxynucleoside using poly(4-vinylpyridine)costyrene

5'-O-4,4'-Dimethoxytrityl-2'-deoxynucleosides have been synthesized in high yield by the reaction of 2'-deoxynucleosides with 4, 4'-dimethoxytrityl chloride in acetonitrile using poly (4-vinylpyridine)-costyrene(styrene 10%).

Dephosphonylation of protected deoxynucleoside and oligodeoxynucleotide H-phosphonates

The conversion of four 5'-O-(4,4'-dimethoxytrityl)-2'- deoxyribonucleoside 3'-H-phosphonates 1 (B=4, 5, 6 and 7) into their partially-protected nucleoside precursors 3 (B=4, 5, 6 and 7, respectively) in good isolated yields is described. The procedure used is also suitable for the dephosphonylation of protected oligonucleotide H-phosphonate blocks.

Nucleoside 5'-methylene phosphonates

Novel oligonucleotides analogs and nucleoside analogs as well as methods for their synthesis are described. The oligonucleotides are useful in diagnostic and therapeutic applications. The oligonucleotides are stable to nuclease degradation.

Synthesis and characterization of phosphate-modified DNA-dimers with fluorine as an uncharged ligand

The potential of the dinucleosidylphosphorofluoridates dCpFdG and dApFdT is described. Side products of the phosphoramidite coupling reaction are synthesized and characterized by 31P-NM]R-spectroscopy.

Facile methods to recycle nucleosides during solid phase synthesis of oligonucleotides

Solid phase syntheses of oligonucleotides, using nucleoside phosphoramidites or methylphosphonamidites require a large excess of nucleoside monomers over the hydroxy functions of the growig oligonucleotide chain bound onto the solid phase. The outlined method allows to recover the excess nucleosides. All the protective groups on the sugar and the nucleobase of the monomers are maintained throughout the recycling process.