57048-45-0Relevant articles and documents
Nucleosides and nucleotides. Part 207: Studies in the chemical conversion of the 4-carboxamide group of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside). Application for the synthesis of 1-deazaguanosine
Kojima, Naoshi,Minakawa, Noriaki,Matsuda, Akira
, p. 7909 - 7914 (2007/10/03)
A mild and versatile chemical conversion of the 4-carboxamide group of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) is described. The reaction of protected AICA-riboside with di-tert-butyl dicarbonate gave 5-[N,N-di-(tert-butoxycarbonyl)]-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-i sopropylidene-β-D-ribofuranosyl)imidazole-4-[N,N-di-(tert-butoxycarbonyl)]ca rboxamide in 71% yield. The resulting tetraBoc derivative was treated with sodium methoxide, benzylamine, or acetonitrile anion to give the corresponding methyl ester, N-benzylcarboxamide, or cyanoacetyl products. The 4-cyanoacetylimidazole derivative was converted into 1-deazaguanosine via an intramolecular cyclization. (C) 2000 Elsevier Science Ltd.