Synthesis of Triazole-Linked Glycoconjugates by Copper(I)-Catalyzed Regiospecific Cycloaddition of Alkynes and Azides

Abstract

Several 1,2,3-triazole-linked glycoconjugates were efficiently synthesized via a Cu(I)-mediated 1,3-dipolar cycloaddition with high regiospecificity and yield (≥ 85%), providing a simple and efficient route to synthesize protected and unprotected neoglycoconjugates. Introduction of a spacer between glycosyl moieties and other compounds reduces steric hindrance, promotes yield, and expands the varieties of glycoconjugates to satisfy various needs of biological events. The structures of all the synthesized glycoconjugates were clearly confirmed by infrared(IR), ¹H NMR, ¹³C NMR, elemental analysis (EA), or MS.

Keywords:

• Click chemistry
• 1,3-dipolar cycloaddition
• glycoconjugates
• 1,2,3-triazoles

ACKNOWLEDGMENTS

This work was supported by the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science (No. 04B0021400), the Natural Science Foundation of Shandong Province (No. Z2006B01), and the Scientific and Technical Tackle Key Problem Project of Shandong Province (2006GG2203024).

Notes

^a Isolated yield.

^a Isolated yield.