Journal
NEW JOURNAL OF CHEMISTRY
Volume 43, Issue 15, Pages 5670-5686Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8nj06138f
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Funding
- National Research, Development and Innovation Office of Hungary [K109450]
- EU - European Regional Development Fund [GINOP-2.3.2-15-2016-00008, GINOP-2.3.3-15-2016-00004]
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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-Dglycopyranosyl) 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.
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