Click Chemistry Inspired Synthesis of Hydroxyanthracene Triazolyl Glycoconjugates.
Nishant PandeyPratibha Dwivedinull JyotiMangat SinghDhananjay KumarVinod Kumar TiwariBhuwan B MishraPublished in: ACS omega (2022)
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.