234436-48-7

Basic information

• Product Name: 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine
• Synonyms: 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine
• CAS NO: 234436-48-7
• Molecular Weight: 633.103
• Mol File: 234436-48-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine(234436-48-7)
• EPA Substance Registry System: 9-[3-O-benzoyl-5-O-(triphenylmethyl)-β-D-ribofuranosyl]-6-chloro-9H-purine(234436-48-7)

Safety Data

• Hazardous Substances Data: 234436-48-7(Hazardous Substances Data)

Upstream product

• 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 
• 228243-48-9 6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine 
• 144925-02-0 6-chloro-9-(5′-O-trityl-β-D-ribofuranosyl)purine 
• 98-88-4 benzoyl chloride 
• 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 
• 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 
• 1360874-43-6 [6-⁽¹⁵⁾N]-3'-O-benzoyl-2'-deoxyadenosine 
• 1360874-42-5 [6-⁽¹⁵⁾N]-5'-O-trityl-2'-deoxyadenosine 
• 1360874-41-4 [6-⁽¹⁵⁾N]-3'-O-benzoyl-5'-O-trityl-2'-deoxyadenosine 
• 1360874-40-3 9-(3-O-benzoyl-5-O-trityl-β-D-2-deoxyribofuranosyl)-6-chloropurine 
• 1360874-39-0 9-(3-O-benzoyl-2-O-phenoxythiocarbonyl-5-O-trityl-β-D-ribofuranosyl)-6-chloropurine 
• 20187-82-0 9-(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 
• 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 
• 110143-10-7 iodenosine 

Relevant articles and documents

INHIBITORS OF E1 ACTIVATING ENZYMES

This invention relates to compounds that inhibit El activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

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.

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.