69471-43-8

Basic information

• Product Name: 6-bis(ethoxycarbonyl)methyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-purine
• Synonyms: 6-bis(ethoxycarbonyl)methyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-purine
• CAS NO: 69471-43-8
• Molecular Weight: 722.708
• Mol File: 69471-43-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-bis(ethoxycarbonyl)methyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bis(ethoxycarbonyl)methyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-purine(69471-43-8)
• EPA Substance Registry System: 6-bis(ethoxycarbonyl)methyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-purine(69471-43-8)

Safety Data

• Hazardous Substances Data: 69471-43-8(Hazardous Substances Data)

Upstream product

• 69359-20-2 6-methylsulfonyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-purine 
• 105-53-3 diethyl malonate 
• 6741-90-8 2',3',5'-tri-O-benzoyl-6-thioinosine 
• 66782-10-3 tri-O-benzoyl-1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose 

Downstream Products

• 16006-62-5 6-ethyl-9-β-D-ribofuranosylpurine 
• 69359-27-9 6-n-propyl-9-β-D-ribofuranosylpurine 
• 14675-48-0 6-methyl-9-(β-D-ribofuranosyl)purine 
• 69359-22-4 6-[2-(ethoxycarbonyl)methyl]-9-(β-D-ribofuranosyl)-9H-purine 

Relevant articles and documents

Reaction of 6-Methylsulfonylpurine Riboside with Carbon Nucleophiles and the Synthesis of 6-Alkylpurine Nucleosides. (Nucleosides and Nucleotides. XXIX)

Treatment of 6-methylsulfonyl-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine with ethyl acetoacetate and sodium hydride in tetrahydrofuran afforded, after deblocking, 6-ethoxycarbonylmethyl-9-β-D-ribofuranosylpurine.Similarly, replacement of the 6-methylsulfonyl moiety with other carbanions derived from diethyl malonate, ethyl cyanoacetate, malononitrile, nitromethane, and sodium cyanide gave the corresponding 6-C-substituted purine nucleosides.Most of these derivatives exist as the 6-(1H)-exomethylene tautomeric forms. 6-Ethoxycarbonylmethylpurine riboside was further converted to 6-methyl, ethyl, propyl, butyl, and pentyl-purine ribosides by decarboxylation or prior alkylation of the methylene group followed by de-carboxylation.This reaction sequence facilitated the preparation of hitherto almost inaccessible alkyl or C-substituted purine nucleosides.Keywords- nucleophilic aromatic substitution; carbon nucleophiles; purine nucleosides; UV; NMR; tautomerism