Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
| Autor: | Tibor Kurtán, Attila Mándi, László Somsák, Sándor Kun, Katalin E. Szabó |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Models
Molecular Circular dichroism Magnetic Resonance Spectroscopy Stereochemistry Pharmaceutical Science 010402 general chemistry Ring (chemistry) 01 natural sciences Article thiazolinone Analytical Chemistry Adduct lcsh:QD241-441 Természettudományok lcsh:Organic chemistry TDDFT-ECD Drug Discovery Moiety glucose derivative Physical and Theoretical Chemistry Kémiai tudományok Molecular Structure 010405 organic chemistry Chemistry Circular Dichroism Monosaccharides Organic Chemistry Absolute configuration Stereoisomerism Time-dependent density functional theory spiro compound 0104 chemical sciences Chemistry (miscellaneous) Thiazolidines Molecular Medicine Density functional theory Formamides |
| Zdroj: | Molecules; Volume 22; Issue 10; Pages: 1760 Molecules, Vol 22, Iss 10, p 1760 (2017) Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules22101760 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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