A Regiospecific and Stereoselective Rearrangement of a 1-β-D-Ribofuranosyl-5-aminoimidazole to a 4-β-D-Ribofuranosylaminoimidazole

David F. Ewing School of Chemistry, University of Hull, Hull, HU6 7RX, UK.

Graharne Mackenzie School of Chemistry, University of Hull, Hull, HU6 7RX, UK.

Sean P. N. Rouse School of Chemistry, University of Hull, Hull, HU6 7RX, UK.

Richard M. Scrowston School of Chemistry, University of Hull, Hull, HU6 7RX, UK.

Abstract

Ethyl 1-methyl-4-(β-D-ribofuranosylamino)imidazole-5-carboxylate 8 was synthesized from ethyl 5-amino-1-(5-O-trityl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxylate 4 by quaternization and subsequent base-catalysed ring-opening and closure.

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A Regiospecific and Stereoselective Rearrangement of a 1-β-D-Ribofuranosyl-5-aminoimidazole to a 4-β-D-Ribofuranosylaminoimidazole

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A Regiospecific and Stereoselective Rearrangement of a 1-β-D-Ribofuranosyl-5-aminoimidazole to a 4-β-D-Ribofuranosylaminoimidazole

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