207347-42-0

Basic information

• Product Name: 3'-DA CEP
• Synonyms: 3'-DA CEP;N6-BENZOYL-5'-O-(4,4'-DIMETHOXYTRITYL)-3'-DEOXYADENOSINE, 2'-[(2-CYANOETHYL)-(N,N-DIISOPROPYL)]PHOSPHORAMIDITE;N6-Benzoyl-5'-O-DMT-3'-deoxyadenosine 2'-CE phosphoramidite;N6-Benzoyl-5'-O-DMT-3'-deoxyadenosine 2'-CE phosphoraMidite;N6-Bz-5'-O-DMTr-3'-deoxyadenosine-2'-O-CED-phosphoramidite;3'-Deoxy-A(Bz)-2'-phosphoramidite
• CAS NO: 207347-42-0
• Molecular Formula: C₄₇H₅₂N₇O₇P
• Molecular Weight: 857.93
• Mol File: 207347-42-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-DA CEP(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-DA CEP(207347-42-0)
• EPA Substance Registry System: 3'-DA CEP(207347-42-0)

Safety Data

• Hazardous Substances Data: 207347-42-0(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 207347-40-8 Acetic acid (2R,3R,5S)-2-(6-benzoylamino-purin-9-yl)-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 
• 207347-41-9 N-{9-[(2R,3R,5S)-5-((R)-1,2-Dihydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 
• 60855-35-8 6-benzoylamino-9-trimethylsilylpurine 
• 76902-49-3 N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 73-03-0 cordycepin 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 84138-86-3 N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 

Downstream Products

• 486424-67-3 N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester 
• 486424-66-2 N⁶-benzoyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester 

Relevant articles and documents

Inhibition of HIV-1 Replication by Chemically Synthesized, Nuclease-Resistant, Nontoxic (2'->5')-Oligoadenylate Agonists

The chemical syntheses of nuclease-resistant, nontoxic bioactive (2'-5')agonists, 3'-deoxyadenylyl-(2'->5')-3'-deoxyadenylyl-(2'->5')-3'-deoxyadenylyl-(2'->2")-9-[(2"-hydroxyethoxy)methyl]adenine (d3A-d3A-d3A-etherA; 36), 1-benzyl-3'-deoxyadenylyl-(2'->5')-3'-deoxyadenylyl-(2'->5')-3'-deoxyadenylyl-(2'->2")-9-[2"-hydroxyethoxy)methyl]adenine (N1-benzyl-d3A-d3A-d3A-etherA; 37), N6-benzyl-3'-deoxyadenylyl-(2'->5')-3'-deoxyadenylyl-(2'->5')-3'-deoxyadenylyl-(2'->2")-9-[(2"-hydroxyethoxy)methyl]adenine (N6-benzyl-d3A-d3A-d3A-etherA; 38), N6-benzyladenylyl-(2'->5')-adenylyl-(2'->5')-adenylyl-(2'->2")-9-[(2"-hydroxyethoxy)methyl]adenine (N6-benzyl-A-A-A-etheA; 39), as well as the biological activities of 37, 38, and already synthesized and published adenylyl-(2'->5')-adenylyl-(2'->5')-adenylyl-(2'->2")-9-[(2"-hydroxyethoxy)methyl]adenine (A-A-A-etherA; 40), are described. The above (2'-5')A derivatives 37-40 inhibit HIV-1 replication as measured by inhibition of syncytia formation, HIV-1 reverse transcriptase activity, or HIV-1 p24-antigen expression, with no evidence of cytotoxicity. Oligonucleotides 37, 38, and 40 were taken up intact into T cells in culture of cytoplasmic concentrations sufficient to activate the latent endoribonuclease, RNase L. N6-Benzyl-d3A-d3A-d3A-etherA (38) also exerts immunostimulatory effects by increasing expression of monocyte chemotactic protein-1 (MCP-1), and thereby, competing with HIV-1 for binding to a critical HIV-coreceptor.