Synthesis of 5′-O-β-d-glucopyranosyl and 5′-O-β-d-galactopyranosyl derivatives of ribavirin

Add time:08/28/2019    Source:sciencedirect.com

The synthesis of 5′-O-β-d-glucopyranosyl and 5′-O-β-d-galactopyranosyl derivatives (13 and 15, respectively) of the antiviral agent ribavirin are descrobed. Direct glycosylation of 2′,3′-O-isopropylideneribavirin with either tetra-O-acetyl-α-d-glucopyranosyl bromide (4) or tetra-O-acetyl-α-d-galactopyranosyl bromide (8) under Koenigs-Knorr conditions (i.e., silver carbonate, silver perchlorate, and Drierite in dichloromethane) followed by O-deacetylation of the reaction product gave the corresponding ortho esters. However, treatment of 2′,3′-di-O-acetyl-5′-O-tritylribavirin (11) with 4 under the Bredereck modification of the Koenigs-Knorr reaction (i.e., silver perchlorate and Drierite in nitromethane) and subsequent deacetylation furnished the desired 1(5-O-β-d-glucopyranosyl-β-d-ribofuranosyl)-1,2,4-triazole-3-carboxamide (13). Similarly, reaction of 11 with 8 in the presence of AgClO4, and deprotection of the condensation product, gave 5′-O-β-d-galactopyranosylribavirin (15). The β-anomeric configuration of the d-glucosyl and d-galactosyl groups of 13 and 15 was assigned by 1H-n.m.r. studies.

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