234436-50-1

Upstream product

• 288-32-4 1H-imidazole 
• 234436-48-7 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine 
• 98-88-4 benzoyl chloride 
• 239811-12-2 Benzoic acid (2R,3R,4R,5R)-2-(6-chloro-purin-9-yl)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 76-83-5 trityl chloride 
• 144925-02-0 6-chloro-9-(5′-O-trityl-β-D-ribofuranosyl)purine 
• 228243-48-9 6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine 
• 2004-06-0 6-Chloropurine riboside 

Downstream Products

• 234436-49-8 9-[3-O-benzoyl-2-deoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]-6-chloro-9H-purine 

Relevant academic research and scientific papers

An industrial process for synthesizing lodenosine (FddA)

Two industrial synthetic approaches to Lodenosine (1, FddA, 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl) adenine) via a purine riboside or a purine 3′-deoxyriboside are described. Several novel applications of deoxygenation and fluorination methods are compared considering reaction yields, economy, safety and environmental concerns.

Improved synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA) using triethylamine trihydrofluoride

An improved synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, FddA) via a fluorination of 3′-O-benzoyl-5′-O-tritylriboside (4a) using noncorrosive triethylamine trihydrofluoride (Et3N·3HF) is described. The method is suitable for large-scale synthesis. In particular, the synthesis of the pivotal intermediate 4a was much improved in avoidance of the use of toxic tin reagent. Radical deoxygenation with several silanes was also studied. The total yield of FddA from 6-chloropurine riboside (2) in this study was greater than that we reported previously.