112233-77-9

Basic information

• Product Name: 2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)-6-O-(diphenylcarbamoyl)guanine
• CAS NO: 112233-77-9
• Molecular Weight: 646.613
• Mol File: 112233-77-9.mol

Chemical Properties

• CAS DataBase Reference: 2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)-6-O-(diphenylcarbamoyl)guanine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)-6-O-(diphenylcarbamoyl)guanine(112233-77-9)
• EPA Substance Registry System: 2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)-6-O-(diphenylcarbamoyl)guanine(112233-77-9)

Safety Data

• Hazardous Substances Data: 112233-77-9(Hazardous Substances Data)

Upstream product

• 112233-74-6 N₂-acetyl-O₆-(diphenylcarbamoyl)guanine 
• 42927-46-8 tetra-O-acetyl-D-xylofuranose 
• 23094-61-3 1,2,3,5-tetra-O-acetyl-β-D-xylofuranose 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 3056-33-5 2,9-diacetylguanine 
• 83-01-2 diphenylcarbamic chloride 

Relevant articles and documents

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.