74465-47-7

Basic information

• Product Name: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• Synonyms: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS NO: 74465-47-7
• Molecular Weight: 457.238
• Mol File: 74465-47-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate(74465-47-7)
• EPA Substance Registry System: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate(74465-47-7)

Safety Data

• Hazardous Substances Data: 74465-47-7(Hazardous Substances Data)

Upstream product

• 7387-57-7 triacetyladenosine 

Downstream Products

• 76513-94-5 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(trifluoromethyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 1867-73-8 N⁶-methyladenosine 
• 30747-21-8 N⁶-benzoyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)adenine 
• 20125-39-7 N6-(2-phenylethyl)adenosine 
• 588698-71-9 5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine 
• 14357-08-5 N-ethyladenosine 
• 14357-07-4 6-Bromo-purine riboside 
• 15981-63-2 2',3',5'-tri-O-acetylnebularine 
• 368421-66-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-(t-butyldimethylsilyl)-9-(β-D-ribofuranosyl)-6-(trifluoromethyl)-purine 
• 368421-65-2 5'-O-(4,4'-dimethoxytrityl)-9-(β-D-ribofuranosyl)-6-(trifluoromethyl)-purine 

Relevant articles and documents

Nucleic acid related compounds. 116. Nonaqueous diazotization of aminopurine nucleosides. Mechanistic considerations and efficient procedures with tert-butyl nitrite or sodium nitrite

Nonaqueous diazotization-dediazoniation of two types of aminopurine nucleoside derivatives has been investigated. Treatment of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine (1) with SbCl3/CH2Cl2 was examined with benzyltriethylammonium (BTEA) chloride as a soluble halide source and tert-butyl nitrite (TBN) or sodium nitrite as the diazotization reagent. Optimized yields (>80%) of the 2,6-dichloropurine derivative were obtained with SbCl3. Combinations with SbBr3/CH2Br2 gave the 2-bromo-6-chloropurine product (>60%), and SbI3/CH2I2/THF gave the 2-iodo-6-chloropurine derivative (>45%). Antimony trihalide catalysis was highly beneficial. Mixed combinations (SbX3/CH2X′2; X/X′ = Bt/Cl) gave mixtures of 2-(bromo, chloro, and hydro)-6- chloropurine derivatives that were dependent on reaction conditions. Addition of iodoacetic acid (IAA) resulted in diversion of purine radical species into a 2-iodo-6-chloropurine derivative with commensurate loss of other radical-derived products. This allowed evaluation of the efficiency of SbX3-promoted cation-derived dediazoniations relative to radical-derived reactions. Efficient conversions of adenosine, 2′-deoxyadenosine, and related adenine nucleosides into 6-halopurine derivatives of current interest were developed with analogous combinations.