Synthesis of certain exocyclic thiazole nucleosides related to tiazofurin. Formation of a unique acycloaminonucleoside

…, SB Larson, RK Robins, GR Revankar…

Index: Sanghvi, Yogesh S.; Larson, Steven B.; Robins, Roland K.; Revankar, Ganapathi R.; Gupta, Pranab K.; et al Journal of Heterocyclic Chemistry, 1988 , vol. 25, p. 623 - 633

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Citation Number: 8

Abstract

Abstract Several thiazole nucleosides structurally related to tiazofurin (1) and ARPP (2) were prepared, in order to determine whether these nucleosides had enhanced antitumor/antiviral activities. Ring closure of 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) thiourea (4) with ethyl bromopyruvate (5a) gave ethyl 2-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosylamino) thiazole-4- carboxylate (6a). Treatment of 6a with sodium methoxide furnished methyl 2-(β-D- ...