Synthesis of Triazole-Linked Glycoconjugates by Copper(I)-Catalyzed Regiospecific Cycloaddition of Alkynes and Azides
- 29 January 2009
- journal article
- research article
- Published by Taylor & Francis Ltd in Synthetic Communications
- Vol. 39 (5), 830-844
- https://doi.org/10.1080/00397910802431198
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
This publication has 30 references indexed in Scilit:
- Synthesis of azide/alkyne-terminal polymers and application for surface functionalisation through a [2 + 3] Huisgen cycloaddition process, “click chemistry”Soft Matter, 2007
- Iterative Glycosylation of 2‐Deoxy‐2‐aminothioglycosides and Its Application to the Combinatorial Synthesis of Linear OligoglucosaminesAngewandte Chemie, 2004
- A Potent and Highly Selective Inhibitor of Human α-1,3-Fucosyltransferase via Click ChemistryJournal of the American Chemical Society, 2003
- GLYCOSYLTRANSFERASES IN OLIGOSACCHARIDE SYNTHESISJournal of Carbohydrate Chemistry, 2002
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie, 2002
- Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to AzidesThe Journal of Organic Chemistry, 2002
- Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective GlycosylationsOrganic Letters, 2001
- Glycosylation and the Immune SystemScience, 2001
- Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligandsNature, 2000
- Biological roles of oligosaccharides: all of the theories are correctGlycobiology, 1993