84915-33-3

Upstream product

• 51549-30-5 5'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 793-10-2 p-nitrophenyl phenyl phosphorochloridate 
• 94189-85-2 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester 4-nitro-phenyl ester phenyl ester 
• 84915-31-1 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 4-nitro-phenyl ester phenyl ester 
• 51549-31-6 3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 

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.

A CONVENIENT METHOD FOR THE FORMATION OF INTERNUCLEOTIDE LINKAGE

Internucleotide linkage can be made readily by reaction of N-unprotected nucleosides and phosphorochloridates or p-nitrophenyl phosphates by the assistance of Grignard reagents.

FACILE NUCLEOSIDE PHOSPHORYLATION VIA HYDROXYL ACTIVATION

A rapid preparation of nucleoside phosphates under very mild conditions is described.