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Issue 15, 2019
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Thio-click reaction of 2-deoxy-exo-glycals towards new glycomimetics: stereoselective synthesis of C-2-deoxy-d-glycopyranosyl compounds

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Abstract

A series of 2-deoxy-glycopyranosyl cyanides with D-arabino, D-lyxo, D-erythro, and D-threo configurations was synthesized from the corresponding glycals via 2-deoxy-glycopyranosyl acetates. The cyanides were transformed to anhydro-aldose tosylhydrazones by reduction with NaH2PO2/Ra-Ni in the presence of tosylhydrazine. The tosylhydrazones furnished 2-deoxy-exo-glycals under modified Bamford–Stevens conditions. Photoinitiated thiol–ene additions of these exo-glycals resulted in the corresponding C-(2-deoxy-D-glycopyranosyl)methyl sulfides in medium to good yields with exclusive regio- and stereoselectivities in most cases. Several disaccharide mimics with a C–S moiety in place of the glycosidic oxygen were also obtained.

Graphical abstract: Thio-click reaction of 2-deoxy-exo-glycals towards new glycomimetics: stereoselective synthesis of C-2-deoxy-d-glycopyranosyl compounds

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Article information


Submitted
04 Dec 2018
Accepted
13 Mar 2019
First published
18 Mar 2019

New J. Chem., 2019,43, 5670-5686
Article type
Paper

Thio-click reaction of 2-deoxy-exo-glycals towards new glycomimetics: stereoselective synthesis of C-2-deoxy-D-glycopyranosyl compounds

J. József, L. Juhász and L. Somsák, New J. Chem., 2019, 43, 5670
DOI: 10.1039/C8NJ06138F

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