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Issue 7, 2016
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A versatile glycosylation strategy via Au(III) catalyzed activation of thioglycoside donors

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Abstract

Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility with substrates having alkenes and the requirement of a stoichiometric amount of promoters, co-promoters and extreme temperatures are some of the limitations. We have developed an efficient methodology for glycosylation via the activation of thioglycoside donors using a catalytic amount of AuCl3 and without any co-promoter. The reaction is very fast, high-yielding and very facile at room temperature. The versatility of this method is evident from the facile glycosylation with both armed and disarmed donors and sterically demanding substrates (acceptors/donors) at ambient conditions, from the stability of the common protecting groups, and from the compatibility of alkene-containing substrates during the reaction.

Graphical abstract: A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors

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Publication details

The article was received on 10 Feb 2016, accepted on 04 Mar 2016 and first published on 08 Mar 2016


Article type: Edge Article
DOI: 10.1039/C6SC00633G
Chem. Sci., 2016,7, 4259-4263
  • Open access: Creative Commons BY license
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    A versatile glycosylation strategy via Au(III) catalyzed activation of thioglycoside donors

    A. M. Vibhute, A. Dhaka, V. Athiyarath and K. M. Sureshan, Chem. Sci., 2016, 7, 4259
    DOI: 10.1039/C6SC00633G

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