Synthesis of 1,2,3-Triazole and Tetrazole Appended Glycoconjugates Based on 3,6-Anhydroglucofuranose via Click Reaction.

ABSTRACT: Synthesis of O-glycosyl 1,2,3-triazoles and tetrazole based on the 3,6-anhydro-β-d-glucofuranoside core of natural sauropunols is reported herein. Toward the objective, O-glycosyl alkynes and nitriles, derived from easily available 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-α- d-glucofuranose using three different alcohols under the modified methanolysis procedure, were subjected to a click reaction using organic and inorganic azides. Subsequent introduction of azido and acetamido groups at C-2 of the sugar moiety and appropriate deprotection reactions involving excellent functional group tolerance with high stereo- and regioselectivity furnished ten 1,4-disubstituted and one 4-substituted 1,2,3-triazoles along with a 5-substituted tetrazole derivative

SUBMITTER: Das S 

PROVIDER: S-EPMC12423807 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature