CHEMOSELECTIVE SYNTHESIS OF 3,6,7-TRISUBSTITUTED 2-(2,3:5,6-DI-<i>O</i>-ISOPROPYLIDENE-β-D-MANNOFURANOSYLOXY]- AND 2-(2-ACETAMIDO-3,4,6-TRI-<i>O</i>-ACETYL-2-DEOXY-β-D-GLUCOPYRANOSYLOXY)QUINOXALINE DERIVATIVES
DOI:
https://doi.org/10.1007/2046Keywords:
glucopyranose, β-glycosides, mannofuranose, quinoxaline O-nucleosides, chemoselective alkylationAbstract
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
