A straightforward route to hydantocidin analogues with pyranose ring structure

Erzsébet Osz, Erzsébet Sós, László Somsák, László Szilágyi, Zoltán Dinya

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Partial hydrolysis of the nitrile moiety in aeetylated 1-bromo-glycopyranosyl cyanides 1 and 9 mediated by TiCl4 gave C-(1-bromo-1-deoxy-glycopyranosyl) formamides 2 and 10 whose reaction either with AgOCN, AgSCN or KSCN in nitromethane resulted in the formation of glycopyranosylidene-spirohydantoins 3, 11 and 15 and -thiohydantoins 7 and 16. Zemplen-deacetylation gave the pyranoid epihydantocidin analogues 4 and 12, and thiohydantocidin analogues 8 and 17, respectively.

Original languageEnglish
Pages (from-to)5813-5824
Number of pages12
JournalTetrahedron
Volume53
Issue number16
DOIs
Publication statusPublished - Apr 21 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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