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Molecules 2017, 22(10), 1760; doi:10.3390/molecules22101760

Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations

Department of Organic Chemistry, University of Debrecen, PO Box 400, H-4002 Debrecen, Hungary
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Received: 25 September 2017 / Revised: 18 October 2017 / Accepted: 18 October 2017 / Published: 19 October 2017
(This article belongs to the Special Issue Advances in Spiro Compounds)
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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. View Full-Text
Keywords: spiro compound; thiazolinone; glucose derivative; TDDFT-ECD spiro compound; thiazolinone; glucose derivative; TDDFT-ECD
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Szabó, K.E.; Kun, S.; Mándi, A.; Kurtán, T.; Somsák, L. Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations. Molecules 2017, 22, 1760.

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