69275-14-5

Basic information

• Product Name: ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate
• Synonyms: ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate
• CAS NO: 69275-14-5
• Molecular Weight: 557.646
• Mol File: 69275-14-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate(69275-14-5)
• EPA Substance Registry System: ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate(69275-14-5)

Safety Data

• Hazardous Substances Data: 69275-14-5(Hazardous Substances Data)

Upstream product

• 4060-34-8 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride 
• 21190-16-9 5-amino-1H-imidazole-4-carboxylic acid ethyl ester 
• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 52522-49-3 2,3,5-tri-O-benzyl-1-(4-nitrobenzoyloxy)-D-arabinofuranose 

Downstream Products

• 5536-17-4 arabinosyl adenine 
• 76054-98-3 5-amino-4-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole 
• 7013-16-3 9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one 
• 76054-93-8 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxamide 
• 64239-99-2 ethyl 5-amino-1-β-D-arabinofuranosylimidazole-4-carboxylate 

Relevant articles and documents

Purines, Pyrimidines, and Imidazoles. Part 52. New Syntheses of Some 1-β-D-Arabinofuranosylaminoimidazoles and of Related Purine Nucleosides, including 9-β-D-Arabinofuranosyladenine

Ethyl 5-amino-1-β-D-arabinofuranosylimidazole-4-carboxylate and the corresponding carboxamide have been prepared by reaction of ethyl 5-aminoimidazole-4-carboxylate or the carboxamide, respectively with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride (but not the bromide or iodide) and deblocking.Reaction of the nucleoside ester with formamidine acetate gave 9-β-D-arabinofuranosylhypoxanthine. 5-Amino-4-cyano-1-β-D-arabinofuranosylimidazole obtained by dehydration of the benzylated carboxamide or by direct glycosylation of 5-amino-4-cyanoimidazole and debenzylation of the product, when heated with triethyl orthoformate and ammonia, gave 9-β-D-arabinofuranosyladenine. 2,3,5-Tri-O-benzylarabinofuranosyl chloride with sodium azide, followed by reduction of the glycosyl azide formed with platinic oxide, and condensation of the arabinosylamine produced with ethyl N-(carbamoylcyanomethyl)formimidate gave a mixture of 2,3,5-tri-O-benzyl 1-α- and -β-D-arabinofuranosylimidazole 4-carboxamides.Reduction of the azide with lithium aluminium hydride followed by debenzylation of the product gave, in addition to tho two anomers, 5-amino-1-D-arabinitylimidazole-4-carboxamide.