97205-04-4

Upstream product

• 100-02-7 4-nitro-phenol 
• 4672-45-1 2-chlorophenylphosphoryl dichloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51600-11-4 5'-O-(p-methoxyphenyldiphenylmethyl)adenosine 

Downstream Products

• 139621-78-6 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-bis-O-(t-butyldimethylsilyl)guanosine 
• 139621-79-7 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-bis-O-(t-butyldimethylsilyl)uridine 
• 139621-81-1 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2'-O-t-butyldimethylsilyl-3'-deoxyadenosine 
• 139621-82-2 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-3'-O-t-butyldimethylsilyl-2'-deoxyadenosine 
• 139621-80-0 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-dideoxyadenosine 
• 97205-05-5 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-bis-O-(t-butyldimethylsilyl)adenosine 
• 139621-77-5 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-bis-O-(t-butyldimethylsilyl)cytidine 

Relevant academic research and scientific papers

Practical Synthesis of 2'-5'-Linked Oligoadenylates (2-5A Oligomers)

A general, facile synthesis of 2'-5'-linked oligonucleotides (2-5A oligomers) has been achieved based on the second-order regioselective protection of adenosine, one-pot formation of the 2'-5' internucleotide linkage, and O-selective phosphorylation of N-unblocked nucleosides.Standard t-butyldimethylsilylation of 5'-O-p-methoxytrityladenosine followed by careful recrystallization from a mixture of triethylamine, methanol, ethyl acetate and ether (4:4:5:100 v/v) gives the 3',5'-di-O-protected adenosine in high yield.Magnesium alkoxide-mediated condensation of the 2'-O-free adenosine with o-chlorophenyl p-nitrophenyl phosphorochloridate followed by 2',3'-di-O-t-butyldimethylsilyladenosine produces the N-free and fully O-protected adenylyl(2'-5')adenosine.The resulting adenylyl dimer, after removal of the 5'-O-trityl protector, is elongated to the protected trimeric compound through a similar reaction sequence.Deprotection of the product furnishes the 2-5A core.Condensation of the 5'-O-detritylated core and bis(2,2,2-trichloroethyl) phosphorochloridate assisted by 2,6-lutidine and subsequent oxidation with aqueous iodine produces, after deblocking, 2-5A 5'-monophosphate (p5'A2'p5'pA2'p5'A).The 2-5A 5'-monophosphate is converted into 2-5A 5'-triphosphate (ppp5'A2'p5'A2'p5'A) by reaction with N,N'-carbonyldiimidazole in the presence of triethylamine followed by tributylammonium diphosphate.This procedure allows ready synthesis of 2-5A oligomers and related compounds on a multigram scale.