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Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A series of quinoxaline O-nucleosides, 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl-1-yl)quinoxalines and 2-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines, was prepared by the reaction of 3,6,7-trisubstituted quinoxalin-2(1H)-ones with the corresponding protected α-chlorosugars in the presence of NaH. The reaction proceeded chemoselectively to give products of O-substitution with β-configuration at anomeric carbon, as proved by NMR data. The deprotection of the 1-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines was achieved by stirring in ammonia–methanol mixture to afford free O-quinoxaline nucleoside analogs.

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Authors and Affiliations

  1. Department of Mathematics and Physics, Faculty of Engineering, Port-Said University, Port Said, 41200, Egypt

    Walid Fathalla

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  1. Walid Fathalla
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Correspondence to Walid Fathalla.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 67–72

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Fathalla, W. Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives. Chem Heterocycl Comp 51, 67–72 (2015). https://doi.org/10.1007/s10593-015-1661-1

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