Tetrahedron

Nucleosides and Nucleotides. Part 207: Studies in the Chemical Conversion of the 4-Carboxamide Group of 5-Amino-1-β-d-ribofuranosylimidazole-4-carboxamide ( …

N Kojima, N Minakawa, A Matsuda

Index: Kojima, Naoshi; Minakawa, Noriaki; Matsuda, Akira Tetrahedron, 2000 , vol. 56, # 40 p. 7909 - 7914

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Citation Number: 8

Abstract

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-isopropylidene-β-d-ribofuranosyl) imidazole-4-[N, N-di-(tert-butoxycarbonyl)] carboxamide in 71% yield. The resulting tetraBoc derivative ...