228243-48-9

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 93-97-0 benzoic acid anhydride 
• 98-88-4 benzoyl chloride 

Downstream Products

• 234436-48-7 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine 
• 234436-55-6 9-[2,3-dideoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl]-9H-purine-6-amine 
• 239811-11-1 9-(5-O-trityl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 234436-49-8 9-[3-O-benzoyl-2-deoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]-6-chloro-9H-purine 
• 239811-12-2 Benzoic acid (2R,3R,4R,5R)-2-(6-chloro-purin-9-yl)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 234436-54-5 9-(3-O-phenoxythiocarbonyl-5-O-trityl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 234436-50-1 Benzoic acid (2R,3R,4R,5R)-5-(6-chloro-purin-9-yl)-4-(imidazole-1-sulfonyloxy)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 339196-22-4 5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside 
• 265987-43-7 9-(5-O-trityl-3-O-methylthiothiocarbonyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl) adenine 
• 110143-10-7 iodenosine 
• 35638-82-5 (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol 
• 568584-95-2 9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine 
• 58-61-7 adenosine 

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.

Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group

A facile and practical method to introduce fluorine at the up-side of the 2'-carbon of nucleosides is described. 6-Chloropurine riboside 3 was converted to the 3'-O-benzoate 4a via a stannylene complex, then converted to the 3'-O-benzoyl-5'-O-tritylriboside 5a. In the presence of pyridine, migration of the 3'-benzoyl groups of 4a and 5a to 2'-OH was rather slow. Hence, 5a was reacted with diethylaminosulfur trifluoride (DAST) in CH2Cl2 in the presence of pyridine to give the 2'-deoxy-2'-fluoroarabinoside 6 in good yield. The 3'-O-benzoyl-5'-O-trityl protecting system was easy to deprotect selectively. Thus, treatment of 6 with ammonia in MeOH gave the 5'- O-trityl compound 7, which was subjected to esterification with phenyl chlorothionoformate, radical deoxygenation with tris(trimethylsilyl)silane and acid treatment to afford 9-(2,3-dideoxy-2-fluoro-β-D-threo- pentofuranosyl)adenine (FddA) 2. In addition, acid treatment of 7 gave 9-(2- deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (FdaraA) 1.

Introduction of a benzoyl group onto riboside in aqueous solution: One- step synthesis of 6-chloropurine 2',3'-di-O-benzoylriboside

A benzoyl group was introduced onto the 3'-hydroxyl group of 6- chloropurine riboside by treatment with benzoylating agents in the presence of an organic or inorganic base in aqueous solution, in which further reaction gave 6-chloropurine 2',3'-di-O-benzo