30747-22-9

Basic information

• Product Name: N²-acetyl-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)guanine
• Synonyms: N²-acetyl-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)guanine
• CAS NO: 30747-22-9
• Molecular Weight: 451.393
• Mol File: 30747-22-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N²-acetyl-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)guanine(CAS DataBase Reference)
• NIST Chemistry Reference: N²-acetyl-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)guanine(30747-22-9)
• EPA Substance Registry System: N²-acetyl-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)guanine(30747-22-9)

Safety Data

• Hazardous Substances Data: 30747-22-9(Hazardous Substances Data)

Upstream product

• 30747-23-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 59278-00-1 2-acetoxyethyl acetoxymethyl ether 
• 3056-33-5 2,9-diacetylguanine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 134222-17-6 C₁₆H₃₁N₅O₂Si₃ 

Downstream Products

• 30747-23-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 75128-73-3 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one 
• 91702-60-2 7-<(2-acetoxyethoxy)methyl>-N²-acetylguanine 
• 2958-98-7 3-methylguanine 
• 185610-61-1 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-7-yl)-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Tautomerism and regioselectivity in ribosylation of guanine

N2-acetyl- and 9,N2-diacetylguanines were subjected to reaction with tetraacetylribose in the presence of p-toluenesulfonic acid. Unlike the ribosylation of diacetylguanine, which gives 7-riboside as a kinetic product, the reaction of monoacetylguanine produces directly a mixture of 7- and 9-ribosides. This reflects N7H right arrow-left arrow N9H tautomerism of the guanine substrate and supports the hypothesis that only the unsubstituted nitrogens of the imidazolium portion of guanine (either N7 or N9) react directly with a sugar cation.

Nucleic acid related compounds. 93. A solution for the historic problem of regioselective sugar-base coupling to produce 9-glycosylguanines or 7-glycosylguanines

Per(trimethylsilyl)-2-N-acylguanine derivatives and tetra-O-acylpentofuranoses were coupled [tin(IV) chloride or titanium(IV) chloride catalysis] to give predominant formation of 7-glycosylguanines. With TiCl4, a fortuitous organic/aqueous partitioning allowed isolation of 7-glycosylguanines from the 7/9 isomer mixtures. Per(trimethylsilyl)-2-N-acyl-6-O-(diphenylcarbamoyl)guanine derivatives and tetra-O-acylpentofuranoses underwent regioselective coupling (trimethylsilyl trifluoromethanesulfonate catalysis) to give 9-glycosylguanines. The 6-O-(diphenylcarbamoyl)peracyl-9-β-D-ribofuranosyl isomer was shown to be both the xinetic and thermodynamic coupling product. Deprotection of all of the peracyl coupling products was effected under mild conditions to give good to high yields of guanine nucleoside analogues. These methodologies provide solutions for the regioselective synthesis of 7- and 9-glycosylguanine nucleosides.