Click Chemistry Inspired Synthesis of Hydroxyanthracene Triazolyl Glycoconjugates

Abstract

Novel hydroxyanthracene-based terminal alkynes 3 and 5a/b were synthesized by the acetylide addition reaction at the 9,10-position of anthraquinone 1 under mild conditions. The developed alkynes 3, 5a, and 5b on Huisgen azide-alkyne cycloaddition reaction with azido-sugars 6 in the presence of Cu(I) catalyst provided a series of triazole fasten hydroxyanthracene glycoconjugates 7, 8, and 9, respectively, in good yields. The representative compounds 9 and 7h were successfully deprotected under room-temperature conditions to liberate the corresponding free glycoconjugates 10 and 11, respectively. Further, structures of a few compounds were unmaliciously evidenced by their single-crystal X-ray. © 2016 American Chemical Society.