339196-22-4

Basic information

• Product Name: 5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside
• Synonyms: 5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside
• CAS NO: 339196-22-4
• Molecular Weight: 765.166
• Mol File: 339196-22-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside(339196-22-4)
• EPA Substance Registry System: 5'-O-trityl-3'-O-benzoyl-2'-O-trifluoromethanesulfonyl-6-chloropurine riboside(339196-22-4)

Safety Data

• Hazardous Substances Data: 339196-22-4(Hazardous Substances Data)

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 
• 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 
• 98-88-4 benzoyl chloride 
• 2004-06-0 6-Chloropurine riboside 

Downstream Products

• 110143-10-7 iodenosine 
• 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 
• 265987-43-7 9-(5-O-trityl-3-O-methylthiothiocarbonyl-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 
• 239811-11-1 9-(5-O-trityl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 234436-55-6 9-[2,3-dideoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl]-9H-purine-6-amine 
• 234436-49-8 9-[3-O-benzoyl-2-deoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]-6-chloro-9H-purine 

Relevant articles and documents

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.

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.