Literature DB >> 19422247

Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synthesis.

Michele Fiore1, Alberto Marra, Alessandro Dondoni.   

Abstract

The high efficiency and selectivity of the thiol-ene radical reaction has been validated by the photoinduced coupling of anomeric sugar thiols with sugar alkenes to give 1,6-linked S-disaccharides in good to excellent yields (76-92%) and high diastereoselectivities (up to 99%). The reaction appears to be well-qualified as an exemplar click process.

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Year:  2009        PMID： 19422247     DOI： 10.1021/jo900514w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

1.  On-resin peptide macrocyclization using thiol-ene click chemistry.

Authors:  Alex A Aimetti; Richard K Shoemaker; Chien-Chi Lin; Kristi S Anseth
Journal:  Chem Commun (Camb)       Date:  2010-04-08       Impact factor: 6.222

2.  Rapid assembly of a library of lipophilic iminosugars via the thiol-ene reaction yields promising pharmacological chaperones for the treatment of Gaucher disease.

Authors:  Ethan D Goddard-Borger; Michael B Tropak; Sayuri Yonekawa; Christina Tysoe; Don J Mahuran; Stephen G Withers
Journal:  J Med Chem       Date:  2012-03-06       Impact factor: 7.446

3.  Exhaustive glycosylation, PEGylation, and glutathionylation of a [G4]-ene(48) dendrimer via photoinduced thiol-ene coupling.

Authors:  Mauro Lo Conte; Maxwell J Robb; Yvonne Hed; Alberto Marra; Michael Malkoch; Craig J Hawker; Alessandro Dondoni
Journal:  J Polym Sci A Polym Chem       Date:  2011-10-15       Impact factor: 2.702

4.  Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking.

Authors:  Dewey A Sutton; Seok-Ho Yu; Richard Steet; Vladimir V Popik
Journal:  Chem Commun (Camb)       Date:  2015-11-05       Impact factor: 6.222

5.  Photoinitiated Thiol-ene Reactions of Enoses: A Powerful Tool for Stereoselective Synthesis of Glycomimetics with Challenging Glycosidic Linkages.

Authors:  Anikó Borbás
Journal:  Chemistry       Date:  2020-03-19       Impact factor: 5.236

6.  Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside.

Authors:  Nathalie Berthet; Bastien Doumeche; Michele Fiore; Dimitri Fayolle; Olivier Renaudet; Peter Strazewski
Journal:  Beilstein J Org Chem       Date:  2019-04-17       Impact factor: 2.883

7.  Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo- and Pentopyranosyl d- and l-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study.

Authors:  Viktor Kelemen; Miklós Bege; Dániel Eszenyi; Nóra Debreczeni; Attila Bényei; Tobias Stürzer; Pál Herczegh; Anikó Borbás
Journal:  Chemistry       Date:  2019-10-01       Impact factor: 5.236

8.  Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols.

Authors:  Tamashree Ghosh; Abhishek Santra; Anup Kumar Misra
Journal:  Beilstein J Org Chem       Date:  2013-05-22       Impact factor: 2.883

9.  The photochemical thiol-ene reaction as a versatile method for the synthesis of glutathione S-conjugates targeting the bacterial potassium efflux system Kef.

Authors:  Jess Healy; Tim Rasmussen; Samantha Miller; Ian R Booth; Stuart J Conway
Journal:  Org Chem Front       Date:  2016-02-26       Impact factor: 5.281

10.  Stereoselective Synthesis of Carbon-Sulfur-Bridged Glycomimetics by Photoinitiated Thiol-Ene Coupling Reactions.

Authors:  Magdolna Csávás; Dániel Eszenyi; Erika Mező; László Lázár; Nóra Debreczeni; Marietta Tóth; László Somsák; Anikó Borbás
Journal:  Int J Mol Sci       Date:  2020-01-16       Impact factor: 5.923
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