69504-05-8

Upstream product

• 69504-04-7 5'-O-(monomethoxytrityl)-2'-O-<(tert-butyl)dimethylsilyl>adenosine 
• 58-61-7 adenosine 
• 14470-28-1 mono-4-methoxytrityl chloride 
• 112208-58-9 2'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 112141-41-0 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51600-11-4 5'-O-(p-methoxyphenyldiphenylmethyl)adenosine 

Downstream Products

• 69504-04-7 5'-O-(monomethoxytrityl)-2'-O-<(tert-butyl)dimethylsilyl>adenosine 
• 75666-61-4 4-Oxo-pentanoic acid (2R,3R,4R,5R)-2-(6-amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 15397-13-4 3'-methyl-adenosine 
• 15397-13-4 9-(3'-C-methyl-β-D-xylo-furanosyl)adenine 
• 125682-12-4 Acetic acid (2R,3R,4S,5R)-2-(6-amino-purin-9-yl)-4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-methyl-tetrahydro-furan-3-yl ester 
• 125682-06-6 9-<5'-O-(4-monomethoxytrityl)-2'-O-t-butyldimethylsilyl-β-D-erythro-pentofuran-3'-ulosyl>adenine 
• 125682-07-7 9-<2'-O-t-butyldimethylsilyl-3'-C-methyl-5'-O-monomethoxytrityl-β-D-xylofuranosyl>adenine 
• 125682-08-8 9-<2'-O-t-butyldimethylsilyl-3'-C-methyl-5'-O-monomethoxytrityl-β-D-ribofuranosyl>adenine 
• 125682-11-3 (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-methyl-tetrahydro-furan-3,4-diol 
• 139621-77-5 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-bis-O-(t-butyldimethylsilyl)cytidine 
• 97205-05-5 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-bis-O-(t-butyldimethylsilyl)adenosine 
• 139621-80-0 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-2',3'-dideoxyadenosine 
• 139621-82-2 o-chlorophenyl 3'-O-t-butyldimethylsilyladenylyl(2'-5')-3'-O-t-butyldimethylsilyl-2'-deoxyadenosine 

Relevant academic research and scientific papers

Nucleotides. Part XL. Synthesis and characterization of modified 2'-5' adenylate trimers - Potential antiviral agents

2'-5' Adenylate trimers 41-44 carrying the (tert-butyl)dimethylsilyl (tbds) group at the 3'-OH position of various sugar moieties were synthesized via the phosphoramidite method. The use of the (tert-butyloxy)carbony (boc) and (2-(4-nitrophenyl)ethylsulfo

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.

Synthesis and Conformation of 9-(3'-C-Methyl-β-D-xylo-furanosyl)adenin and 3-C'-Methyladenosine, Two Sugar-Methylated Nucleoside Analogues

A novel synthetic route for the sugar-methylated nucleoside analogue 9-(3-C'-methyl-β-D-xylo-furanosyl)adenine (1) is reported.A Grignard reaction in THF with an appropriately protected keto nucleoside gave the xylo structure 4 in 60percent yield.Using diethyl ether as the solvent, the Grignard reaction furnished compound 4 in 35percent yield, along with the ribo epimer (ca. 1percent).The ribo epimer is the precursor of 3'-C-methyladenosine (2).Compounds 4 and 5 could be conveniently deprotected to obtain the title compounds in good yields.The conformational properties of 1 and 2 were analyzed using 500 MHz 1H NMR spectroscopy.In line with earlier experiments, it is found that the methyl group on the sugar ring strongly prefers an equatorial location.For 1, this results in the predominant population of the North (3T2) puckered form of the sugar ring, whereas compound 2 resides primarily in the South (2T3) conformation.

ISOMERIZATION OF tert-BUTYLDIMETHYLSILYL PROTECTING GROUPS IN RIBONUCLEOSIDES

The tert-butyldimethylsilyl group undergoes isomerization between O-2' and O-3' in ribonucleosides in solution.Isomerization is most rapid in protic solvents and extremely slow in such solvents as dry dimethyl sulfoxide, pyridine, oxolane, chloroform, or

The synthesis of 2′-5′ linked oligoribonucleotides

The use of alkylsilyl protecting groups provides a rapid route to 3′,5′-diprotected ribonucleosides which are easily coupled via the phosphorodichloridite procedure to produce 2′-5′ linked ribonucleotides.