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

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 presenc...

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Bibliographic Details
Published inNew journal of chemistry Vol. 43; no. 15; pp. 5670 - 5686
Main Authors Jozsef, Janos, Juhasz, Laszlo, Somsak, Laszlo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
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Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj06138f