Silver trifluoromethanesulfonate and metallic copper mediated syntheses of 1, 2, 3-triazole-O- and triazolyl glycoconjugates: consecutive glycosylation and cyclization under one-pot condition. Issue 29 (20th July 2016)

• Record Type: Journal Article
• Authors: Dutta, Samrat; Gupta, Shyam Ji; Sen, Asish Kumar
• Is Part Of: Tetrahedron letters. Volume 57:Issue 29(2016)
• Page Start: 3086
• Page End: 3090
• Publication Date: 2016-07-20
• Subjects: 1, 2, 3-Triazole glycoconjugates -- Silver trifluoromethanesulfonate -- Copper -- Consecutive glycosylation–cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.088
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Syntheses of 1, 2, 3-triazole- O - and triazolyl glycoconjugates using AgOTf and Cu(0). One-pot process for consecutive glycosylation and azide alkyne cyclization. The process is rapid and does not require isolation of intermediates. AgOTf acts as promoter for glycosylation and co-catalyst for cyclization reaction. Several 1, 2, 3-triazole- O - and triazolyl glycoconjugates have been synthesized. Abstract: A new protocol for synthesis of 1, 2, 3-triazole glycoconjugates has been described. The reaction involves consecutive glycosylation and azide alkyne cyclization under one-pot condition using a combination of AgOTf and Cu(0) catalyst. Here, AgOTf acts as a promoter for the glycosylation reaction and then as a co-catalyst for the subsequent click reaction.