237410-10-5

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 1824-96-0 methyl xylofuranoside 
• 98-88-4 benzoyl chloride 
• 6022-96-4 5-O-benzoyl-α-D-xylofuranose 
• 551929-54-5 methyl-[O³,O⁵-isopropylidene-O²-(toluene-4-sulfonyl)-β-D-xylofuranoside] 
• 96622-64-9 Methyl-2-O-tosyl-β-D-xylofuranosid 
• 51754-99-5 Methyl 3,5-O-Isopropylidene-β-D-xylofuranoside 
• 43168-73-6 methyl 2,3-anhydro-β-D-lyxofuranoside 
• 152711-00-7 Methyl 3-deoxy-3-fluoro-β-D-arabinofuranoside 
• 532-32-1 sodium benzoate 
• 551929-56-7 Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-fluoro-2-methoxy-tetrahydro-furan-3-yl ester 

Downstream Products

• 112695-36-0 methyl 2,5-di-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside 
• 1434144-22-5 ((2R,3R,5R)-3-fluoro-5-methoxy-4-oxotetrahydrofuran-2-yl)methyl benzoate 
• 1434144-23-6 ((2R,3R,4S,5R)-3-fluoro-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 1434144-24-7 ((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 551929-60-3 C₂₅H₂₁ClFN₅O₅ 
• 551929-59-0 C₃₁H₂₄ClFIN₅O₅ 
• 551929-68-1 Benzoic acid (2R,3S,4S,5R)-2-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-fluoro-5-methylcarbamoyl-tetrahydro-furan-3-yl ester 
• 551929-66-9 (2R,3S,4S,5R)-4-Benzoyloxy-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-3-fluoro-tetrahydro-furan-2-carboxylic acid methyl ester 
• 122654-35-7 C₂₄H₁₇Cl₂FN₄O₅ 
• 551929-65-8 (2R,3S,4S)-5-Acetoxy-4-benzoyloxy-3-fluoro-tetrahydro-furan-2-carboxylic acid methyl ester 
• 551929-64-7 (2R,3S,4S,5R)-4-Benzoyloxy-3-fluoro-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and evaluation of 3′-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents

Kinetoplastid parasites are the causative agents of neglected tropical diseases with an unmet medical need. These parasites are unable to synthesize the purine ring de novo, and therefore rely on purine salvage to meet their purine demand. Evaluating purine nucleoside analogs is therefore an attractive strategy to identify antikinetoplastid agents. Several anti-Trypanosoma cruzi and anti-Trypanosoma brucei 7-deazapurine nucleosides were previously discovered, with the removal of the 3′-hydroxyl group resulting in a significant boost in activity. In this work we therefore decided to assess the effect of the introduction of a 3′-fluoro substituent in 7-deazapurine nucleosides on the anti-kinetoplastid activities. Hence, we synthesized two series of 3′-deoxy-3′-fluororibofuranosyl and 3′-deoxy-3′-fluoroxylofuranosyl nucleosides comprising 7-deazaadenine and -hypoxanthine bases and assayed these for antiparasitic activity. Several analogs with potent activity against T. cruzi and T. brucei were discovered, indicating that a fluorine atom in the 3′-position is a promising modification for the discovery of antiparasitic nucleosides.

Synthesis of 2-fluoro-substituted and 2,6-modified purine 2′,3′-dideoxy-2′,3′-difluoro-D-arabinofuranosyl nucleosides from D-xylose

A series of novel purine-modified 2′,3′-dideoxy-2′,3′-difluro-D-arabinonucleosides, including fluorinated analogs of fludarabine and nelarabine, have been prepared via anion glycosylation reactions of salts of 2-fluoropurine derivatives with the glycosyl bromide. A short and efficient synthetic route to the carbohydrate precursor 5-O-benzoyl-2,3-difluoro-α-D-arabinofuranosyl bromide was developed in five steps from D-xylose. Improved synthesis of methyl 5-O-benzoyl-2,3-difluoro-α-D-arabinofuranoside based upon the study of diethylaminosulfur trifluoride (DAST)-reactions with 5-O-protected methyl D-xylosides was explored using mild reaction conditions on the key step. New peculiarities for selective fluorinations of 5-O-benzoylated α- and β-D-pentofuranosides with DAST leading to the formation of mono and difluoro-furanoside derivatives are reported.

SUBSTITUTED PURINE NUCLEOSIDES, PHOSPHORAMIDATE AND PHOSPHORDIAMIDATE DERIVATIVES FOR TREATMENT OF VIRAL INFECTIONS

This invention is directed to compounds of Formula (I) having the structure that are useful in the treatment of viral infections in mammals, particularly in humans, mediated, at least in part, by a virus in the Flaviviridae family of viruses.

Design and synthesis of A3 adenosine receptor ligands, 3′-fluoro analogues of Cl-IB-MECA

Synthesis of 3′-deoxy-3′-fluoro-N6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A 3 adenosine receptor are described.

Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

Several 3′-fluoro analogues, 1a, 1b, and 1c of selective and potent adenosine A3 receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 8b with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A3 adenosine receptor, the corresponding 3′-fluoro derivative showed remarkably decreased binding affinity, indicating that 3′-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A3 adenosine receptor.

A novel route for the synthesis of deoxy fluoro sugars and nucleosides

The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O- benzoyl-β-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the α-D-ano

A novel route for the synthesis of fluorodeoxy sugars and nucleosides

Ring-fluorination of α- and β-D-pentofuranosides containing free secondary hydroxyl groups by (diethylamino)sulfur trifluoride (DAST) was studied.

Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides

Oxidation of 1a with DMSO-acetic or trifluoroacetic anhydride led to the formation of a mixture of epimeric gem-diols 2 and 3 in the ratios of ?3:1 and ?7:1, respectively. Reduction of this mixture with NaBH4 followed by benzoylation and chroma