Literature DB >> 31278614

Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives.

Monalisa Kundu1, Ishani Bhaumik1, Anup Kumar Misra2.   

Abstract

Organocatalytic coupling of glycosyl azides with enolates of active ketones and esters through azide-enolate [3 + 2] cycloaddition in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives in excellent yield. The reaction condition is simple and can be scaled-up. Graphical abstract Coupling of glycosyl azides with active ketones through azide-enolate [3 + 2] cycloaddition in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives in excellent yield.

Entities:  

Keywords:  Azide; Carbohydrate; triazole; Cycloaddition; Organocatalysis

Mesh：

Substances：

Year:  2019        PMID： 31278614     DOI： 10.1007/s10719-019-09883-1

Source DB:  PubMed          Journal:  Glycoconj J        ISSN： 0282-0080            Impact factor:   2.916


  31 in total

1.  An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition reaction: regioselective high-yielding synthesis of fully decorated 1,2,3-triazoles.

Authors:  Adluri B Shashank; S Karthik; R Madhavachary; Dhevalapally B Ramachary
Journal:  Chemistry       Date:  2014-11-03       Impact factor: 5.236

2.  Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes.

Authors:  Peng Wu; Alina K Feldman; Anne K Nugent; Craig J Hawker; Arnulf Scheel; Brigitte Voit; Jeffrey Pyun; Jean M J Fréchet; K Barry Sharpless; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

3.  Highly enantioselective alpha-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst.

Authors:  Daniel Font; Amaia Bastero; Sonia Sayalero; Ciril Jimeno; Miquel A Pericàs
Journal:  Org Lett       Date:  2007-04-17       Impact factor: 6.005

4.  Surface-initiated, atom transfer radical polymerization of oligo(ethylene glycol) methyl ether methacrylate and subsequent click chemistry for bioconjugation.

Authors:  Bong Soo Lee; Jungkyu K Lee; Wan-Joong Kim; Young Hwan Jung; Sang Jun Sim; Jeewon Lee; Insung S Choi
Journal:  Biomacromolecules       Date:  2007-02       Impact factor: 6.988

5.  Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases.

Authors:  David R da Rocha; Wilson C Santos; Emerson S Lima; Vitor F Ferreira
Journal:  Carbohydr Res       Date:  2012-01-03       Impact factor: 2.104

6.  C-Glucopyranosyl-1,2,4-triazoles As New Potent Inhibitors of Glycogen Phosphorylase.

Authors:  Eva Bokor; Tibor Docsa; Pál Gergely; László Somsák
Journal:  ACS Med Chem Lett       Date:  2013-05-17       Impact factor: 4.345

Review 7.  Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides.

Authors:  Jason E Hein; Valery V Fokin
Journal:  Chem Soc Rev       Date:  2010-03-04       Impact factor: 54.564

Review 8.  In situ click chemistry: probing the binding landscapes of biological molecules.

Authors:  Sreeman K Mamidyala; M G Finn
Journal:  Chem Soc Rev       Date:  2010-03-01       Impact factor: 54.564

Review 9.  The growing impact of click chemistry on drug discovery.

Authors:  Hartmuth C Kolb; K Barry Sharpless
Journal:  Drug Discov Today       Date:  2003-12-15       Impact factor: 7.851

10.  Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates.

Authors:  Fernando de C da Silva; Maria Cecilia B V de Souza; Izabel I P Frugulhetti; Helena C Castro; Silmara L de O Souza; Thiago Moreno L de Souza; Diego Q Rodrigues; Alessandra M T Souza; Paula A Abreu; Fabiana Passamani; Carlos R Rodrigues; Vitor F Ferreira
Journal:  Eur J Med Chem       Date:  2008-03-16       Impact factor: 6.514
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