A practical synthesis of ethyl 1, 2, 4??triazole??3??carboxylate and its use in the formation of chiral 1′, 2′??seco??nucleosides of ribavirin

P Vemishetti, RW Leiby, E Abushanab…

Index: Vemishetti; Leiby; Abushanab; Panzica Journal of Heterocyclic Chemistry, 1988 , vol. 25, # 2 p. 651 - 654

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Citation Number: 13

Abstract

Abstract A practical and efficient synthesis of ethyl 1, 2, 4-triazole-3-carboxylate (6a, R'= H) from ethyl carboethoxyformimidate hydrochloride (7) is described. Alkylation of this heterocycle with the chloromethyl ethers of 1, 3-O-dibenzylbutane-1, 2R, 3S-triol (8a) and 1, 3, 4-O-tribenzylbutane-1, 2R, 3S, 4-tetrol (8b), followed by conversion of the ester function to the amide and deprotection, furnished the chiral 1′, 2′-seco-nucleosides of ribavirin, ...