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Issue 6, 2015
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Sugar silanes: versatile reagents for stereocontrolled glycosylation via intramolecular aglycone delivery

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Abstract

A new method for the intramolecular glycosylation of alcohols is described. Utilizing carbohydrate-derived silanes, the catalytic dehydrogenative silylation of alcohols is followed by intramolecular glycosylation. Appropriate combinations of silane position and protecting groups allow highly selective access to β-manno, α-gluco, or β-gluco stereochemical relationships as well as 2-azido-2-deoxy-β-gluco- and 2-deoxy-β-glucosides. Intramolecular aglycone delivery from the C-2 or C-6 position provides 1,2-cis or 1,2-trans glycosides, respectively. Multifunctional acceptor substrates such as hydroxyketones and diols are tolerated and are glycosylated in a site-selective manner.

Graphical abstract: Sugar silanes: versatile reagents for stereocontrolled glycosylation via intramolecular aglycone delivery

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Publication details

The article was received on 05 Mar 2015, accepted on 12 Apr 2015 and first published on 14 Apr 2015


Article type: Edge Article
DOI: 10.1039/C5SC00810G
Citation: Chem. Sci., 2015,6, 3448-3453
  • Open access: Creative Commons BY license
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    Sugar silanes: versatile reagents for stereocontrolled glycosylation via intramolecular aglycone delivery

    J. T. Walk, Z. A. Buchan and J. Montgomery, Chem. Sci., 2015, 6, 3448
    DOI: 10.1039/C5SC00810G

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