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

János József, László Juhász, László Somsák

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5670-5686
Number of pages17
JournalNew Journal of Chemistry
Volume43
Issue number15
DOIs
Publication statusPublished - Jan 1 2019

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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