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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

Walid Fathalla
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Abstract


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.

How to Cite
Fathalla, W. Chem. Heterocycl. Compd. 2015, 51, 67. [Khim. Geterotsikl. Soedin. 2015, 51, 67.]

For this article in the English edition see DOI 10.1007/s10593-015-1661-1


Keywords


glucopyranose; β-glycosides; mannofuranose; quinoxaline O-nucleosides; chemoselective alkylation

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