Glucopyranosylidene-spiro-thiazolinones: Synthetic studies and determination of absolute configuration by TDDFT-ECD calculations

Katalin E. Szabó, Sándor Kun, Attila Mándi, Tibor Kurtán, László Somsák

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reactions of O-peracylated C-(1-bromo-β-D-glucopyranosyl)formamides with thioamides furnished the corresponding glucopyranosylidene-spiro-thiazolin-4-one. While O-debenzoylations under a variety of conditions resulted in decomposition, during O-deacetylations the addition of MeOH to the thiazolinone moiety was observed, and with EtOH and water similar adducts were isolated or detected. The structure and stereochemistry of the new compounds were established by means of NMR and electronic circular dichroism (ECD) data supported by time-dependent density functional theory ECD (TDDFT-ECD) calculations. TDDFT-ECD calculations could efficiently distinguish the proposed epimeric products having different absolute configuration in the spiro heterocyclic ring.

Original languageEnglish
Article number1760
JournalMolecules
Volume22
Issue number10
DOIs
Publication statusPublished - Oct 2017

Keywords

  • Glucose derivative
  • Spiro compound
  • TDDFT-ECD
  • Thiazolinone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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