339196-22-4

Upstream product

• 421-83-0 trifluoromethane sulfonyl chloride 
• 234436-48-7 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine 
• 98-88-4 benzoyl chloride 
• 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 
• 239811-12-2 Benzoic acid (2R,3R,4R,5R)-2-(6-chloro-purin-9-yl)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-3-yl ester 

Downstream Products

• 234436-49-8 9-[3-O-benzoyl-2-deoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]-6-chloro-9H-purine 
• 110143-10-7 iodenosine 
• 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 
• 234436-54-5 9-(3-O-phenoxythiocarbonyl-5-O-trityl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 265987-43-7 9-(5-O-trityl-3-O-methylthiothiocarbonyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl) adenine 
• 339196-23-5 thiocarbonic acid O-[5-(6-amino-purin-9-yl)-4-fluoro-2-trityloxymethyl-tetrahydro-furan-3-yl] ester O-(4-fluoro-phenyl) ester 

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.

PROCESS FOR PRODUCING NUCLEOSIDE DERIVATIVES

Nucleoside derivatives wherein the hydroxyl group at the 2'-position has been replaced by a fluorine atom, etc. and the hydroxyl group at the 3'-position has been deoxylated, such as 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl) adenine (FddA), etc. and the compounds related thereto can be produced conveniently and at an advantage industrially from a purine riboside, by substituting a halogen atom for the 6-position in the purine riboside, modifying the hydroxyl groups at the 3'-and 5'-positions of the sugar moiety thereof with protecting groups which can not be deprotected (deblocked) under the same condition, further introducing a desired substituent group, such as a fluorine atom, etc. thereinto at the 2'-position of the sugar moiety and then deprotecting (deblocking)-deoxylating the protected hydroxyl group at the 3'-position thereof. Further, processes for producing important intermediates usable in the above production and thus produced novel intermediates are also provided.