19325-87-2

Upstream product

• 938053-00-0 8-fluoro-2',3'-O-(1-methylethylidene)adenosine 
• 938052-99-4 8-fluoro-2',3'-O-(1-methylethylidene)-5'-O-(tetrahydro-2H-pyran-2-yl)adenosine 
• 64-18-6 formic acid 
• 64-19-7 acetic acid 

Downstream Products

• 27963-80-0 1-methyl-8-oxoadenosine 
• 880155-70-4 8-(Biphenyl-4-ylmethylamino)-9-β-D-arabinofuranosyladenine 
• 1423158-40-0 C₃₁H₂₅N₅O₈ 
• 1423158-30-8 6-azido-8-oxo-7,8-dihydropurinoriboside tribenzoate 
• 1423158-59-1 6-chloro-8-oxo-7,8-dihydropururinoriboside tribenzoate 
• 1423158-41-1 8-oxo-7,8-dihydroinosine tribenzoate 
• 297731-15-8 6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite] 
• 297731-13-6 6-N-acetyl-2',3'-di-O-benzoyl-5'-O-tert-butyldimethylsilyl-8-oxoadenosine 
• 297731-14-7 6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 
• 3868-35-7 6-N-acetyl-8-oxoadenosine 
• 439097-89-9 6-N-[(4,4'-dimethoxytrityl)]-2',3'-O-isopropylidene-8-oxoadenosine 5'-(methyl N,N-diisopropylphosphoramidite) 
• 439097-87-7 6-N-[(4,4'-dimethoxytrityl)]-2',3'-O-isopropylidene-8-oxoadenosine 
• 651737-69-8 6-Amino-9-((3aR,4R,6R,6aR)-6-{butoxy-[((S)-1-trityl-pyrrolidine-2-carbonyl)-amino]-phosphoryloxymethyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-8-oxo-8,9-dihydro-purine-7-carboxylic acid tert-butyl ester 
• 660851-80-9 N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-methionyl)phosphoramidate] 

Relevant academic research and scientific papers

The elusive 8-fluoroadenosine: a simple non-enzymatic synthesis and characterization

The only successful synthesis of 8-fluoroadenosine reported until now relied on an enzymatic removal of the acetate protecting groups using thermally resistant hydrolases. In the present communication we describe the first non-enzymatic synthesis of 8-fluoroadenosine. According to this, the C8-fluorine atom was introduced in a halogen-exchange process performed at elevated temperature. The chief obstacle in the synthesis of 8-fluoroadenosine, the removal of the protecting groups in the presence of the labile C8-F bond, was addressed by judicious choice of acid-labile protecting groups. Their deprotection in the presence of C8-F is described. Using this newly developed procedure, significant quantities of 8-fluoroadenosine were synthesized and, for the first time, its physicochemical properties including pH-dependent stability, examined in detail. The intermediate generation of 8-fluoroadenosines as a tool to increase the reaction rates of nucleophilic substitutions was briefly examined and successfully demonstrated with the example of 8-cyanoadenosine. The presented procedure is applicable to the synthesis of various adenosine analogs with potential pharmacological significance.